Month: October 2020

4254-15-3 A common heterocyclic compound, 4254-15-3,(S)-Propane-1,2-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

Example 33 : (2R, 75R)-2-[(l-Aminoisoquinolin-6-yl)amino]-8-fluoro-7- {[(25)-l- hydroxypropan-2-yl]oxy } -4, 15,20-trimethyl- 13 -oxa-4, 1 1- diazatricyclo[14.2.2.16, 10]henicosa-l(18),6,8, 10(21), 16, 19-hexaene-3, 12-dione; trifluoroacetic acid [00356] To a solution of (s)-(+)-l,2-propanediol (2.0 g, 26.3 mmol) in DMF (5 mL) was added TBS-C1 (5.94 g, 39.4 mmol) and imidazole (2.147 g, 31.5 mmol). The reaction was stirred at 25 ¡ãC for 18 h. The reaction mixture was partitioned between ethyl acetate and sat. ammonium chloride. The organic phase was washed with sat. ammonium chloride and brine, dried (MgS04) and concentrated in vacuo. The crude product was purified by flash chromatography to give 33A (4.0 g, 80percent yield) as a colorless oil. 33B: (5)-Benzyl 2-((l-((tert-butyldimethylsilyl)oxy)propan-2-yl)oxy)-3-fluoro-5- nitrobenzyl(methyl)carbamate [00357] To a solution of 27B (400 mg, 1.197 mmol), 33A (251 mg, 1.316 mmol) and triphenylphosphine (345 mg, 1.316 mmol) in THF (10 mL) at 0 ¡ãC, was added DIAD (0.256 mL, 1.316 mmol) dropwise. The reaction mixture was allowed to slowly warm to rt and stirred for 16 h, then was concentrated. The crude product was purified by flash chromatography (0 to 40percent ethyl acetate/hexanes) to give 33B (577 mg, 1.139 mmol, 95percent yield) as colorless oil. MS (ESI) m/z: 507.1 [M+1]+. H MR (400 MHz, chloroform-d) delta ppm 7.78 – 7.94 (2 H, m) 7.27 – 7.43 (5 H, m) 5.17 (2 H, d, J=20.1 Hz) 4.46 – 4.74 (3 H, m) 3.65 – 3.81 (2 H, m) 2.97 (3 H, d, J=15.8 Hz) 1.31 (3 H, t, J=7.0 Hz) 0.81 (9 H, d, J=7.0 Hz) -0.05 – 0.04 (6 H, m) rotamers. 33C: (S)-4-((l-((tert-Butyldimethylsilyl)oxy)propan-2-yl)oxy)-3-fluoro-5- ((methylamino)methyl)aniline [00358] To a degassed solution of 33B (573 mg, 1.131 mmol) in MeOH (10 mL), was added 10percent Pd-C (50 mg, 0.047 mmol). The mixture was evacuated and flushed with H2 (3X), then was stirred under an atmosphere of H2 for 8 h. The mixture was filtered and concentrated to give 33C (382 mg, 1.115 mmol, 99percent yield) as a pale brown oil. MS (ESI) m/z: 343.1 [M+l]+. PI MR (400 MHz, chloroform-d) delta ppm 6.40 (1 H, d, J=1.8 Hz) 6.33 (1 H, dd, J=12.5, 2.8 Hz) 4.20 (1 H, sxt, J=5.7 Hz) 3.62 – 3.79 (4 H, m) 3.53 (2 H, br. s.) 2.40 (3 H, s) 1.25 (3 H, d, J=6.3 Hz) 0.89 (9 H, s) 0.05 (6 H, s). 33D: tert-Butyl N- {6-[({[(5-amino-2- { [(25)- l-[(tert-butyldimethylsilyl)oxy]propan-2- yl]oxy } -3 -fluorophenyl)methyl](methyl)carbamoyl} ( {4-[(2R)- 1 -hydroxypropan-2-yl]-3 – methylphenyl} )methyl)amino]isoquinolin- 1 -yl} -N-[(tert-butoxy)carbonyl]carbamate [00359] To Intermediate 5 (100 mg, 0.515 mmol), Intermediate 1 (185 mg, 0.515 mmol), and glyoxylic acid monohydrate (47.4 mg, 0.515 mmol), were added DMF (6.00 mL) and acetonitrile (6 mL). The mixture was stirred at 80 ¡ãC for 1 h, then was cooled to rt. To the mixture were added sequentially 33C (201 mg, 0.587 mmol), DMF (6.00 mL), TEA (0.215 mL, 1.546 mmol) and BOP (251 mg, 0.567 mmol). The reaction mixture was stirred at rt for 1 h, then was diluted with H20 and extracted with EtOAc (3X). The extract was washed with brine, dried ( a2S04) and concentrated. The crude product was purified by flash chromatography (1 to 15percent MeOH/methylene chloride) to give 33D (422 mg, 0.474 mmol, 92percent yield) as an orange foam. MS (ESI) m/z: 890.3 [M+l]+. H MR: complicated due to presence of diastereomers and amide rotamers. Example 33 [00360] To a solution of 33D (417 mg, 0.468 mmol) in dichloromethane (10 mL) and acetonitrile (5 mL) at 0 ¡ãC, was added phosgene (20percent in toluene, 0.243 mL, 0.492 mmol) dropwise. The mixture was stirred at 0 ¡ãC for 20 min, then was removed from the cooling bath and bubbled with Ar for 20 min. This mixture was added dropwise via a syringe pump into a solution of TEA (0.392 mL, 2.81 mmol) in dichloromethane (190 mL) over 5 h. The reaction mixture was allowed to stir at rt for 11 h, and then concentrated. The crude product was purified by flash chromatography (1 to 15percent MeOH/methylene chloride) to give a mixture of diastereoisomers. The diastereomers were separated by a prep chiral HPLC (R,R-Whelk-0 column 21.1 x 250 mm). The desired fractions were combined and concentrated. The residue was treated with TFA (4 mL) for 15 min. The reaction mixture was concentrated and purified by prep HPLC to give Example 33 (52.9 mg, 0.074 mmol, 31.4percent yield) white solid. MS (ESI) m/z: 602.2 [M+l]+. NMR (400 MHz, methanol-d4) delta ppm 8.05 (1 H, d, J=9.3 Hz) 7.64 (1 H, dd, J=7.8, 1.8 Hz) 7.44 (1 H, d, J=7.8 Hz) 7.31 (1 H, d, J=7.0 Hz) 7.18 – 7.23 (2 H, m) 6.91 (1 H, d, J=7.3 Hz) 6.83 (1 H, d, J=2.3 Hz) 6.53 (1 H, dd, J=12.4, 2.4 Hz) 5.73 (1 H, s) 5.66 (1 H, br. s.) 5.37 (1 H, d, J=17.1 Hz) 4.65 (1 H, t, J=11.0 Hz) 4.27 – 4.38 (1 H, m, J=5.7, 5.7, 5.7, 5.7, 5.4 Hz) 4.06 (1 H, d, J=17.3 Hz) 3.96 (1 H, dd, J=10.8, 4.3 Hz) 3.63 (2 H, d, J=4.8 Hz) 3.43 – 3.55 (1 H, m) 3.27 (3 H, s) 2.34 (3 H, s) 1.30 (3 H, d, J=7.0 Hz) 1.27 (3 H, d, J=6.3 Hz). Analytical HPLC (low pH, 254 nM): Sunfir…

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand 4254-15-3 reaction routes.

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; GLUNZ, Peter W.; PRIESTLEY, Eldon Scott; JOHNSON, James, A.; WURTZ, Nicholas, Ronald; LADZIATA, Vladimir; WO2013/184734; (2013); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

538-58-9,Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 1,5-Diphenylpenta-1,4-dien-3-one,538-58-9, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a solution of DVK 1 (0.2 mmol) and active methylene 2 (0.24 mmol) was addedt-Bu-P2 (10uL, 10 mol%) via a micro syringe at room temperature. The reactionmixture was stirred for 2-24 h as indicated in Table 2. The solvent was then removedin vacuo and the crude product was purified by flash chromatography on silica gel(PE/EA = 15:1-10:1) to give the desired product 3., 538-58-9

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 538-58-9.

Reference£º
Article; Li, Yang-Guo; Zhang, Yang; Du, Guang-Fen; Gu, Cheng-Zhi; He, Lin; Letters in Organic Chemistry; vol. 16; 1; (2019); p. 76 – 80;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact.24621-61-2,(S)-Butane-1,3-diol, it is a common compound, a new synthetic route is introduced below.24621-61-2

Example 4 Synthesis of Maytansinoid 4k,l (d) S-1,3-Di-O-p-toluenesulfonyl-butane 22: A solution of S-(-)-1,3-butanediol (21, 2.00 g (22.22 mmol) in a mixture of dry pyridine (40 mL) and dry toluene (60 mL) was treated with p-toluenesulfonyl chloride (12.70 g, 66.84 mmol) under argon at 0 C. After stirring at 0 C. for 5 min. followed by stirring at room temperature for 2 h, the mixture was evaporated under vacuum. The residue was redissolved in ethyl acetate, washed with 0.1 M aqueous NaHCO3, and saturated NaCl. The organic layer was separated, dried over MgSO4, filtered and evaporated. The residue was purified by chromatography over silica gel, eluding with 1:2 ethyl acetate/hexane to give 6.25 g (71%) of the title product 22 Rf=0.40 (1:1 EtOAc/hexane); 1H NMR (CDCl3) 7.76 (dd, 4H, J=1.0, 8.0 Hz), 7.35 (dt, 4H, J=0.4, 8.0+8.0 Hz), 4.70 (m, 1H), 4.03 (m, 1H), 3.94 (m, 1H), 2.46 (s, 6H), 1.92 (m, 2H), 1.26 (d, 3H, J=6.3 Hz); 13C NMR 145.17, 133.00, 130.11, 128.12, 127.91, 76.28, 66.21, 36.08, 21.86, 21.06; MS: 420.99 (M+Na)+., 24621-61-2

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles. 24621-61-2, other downstream synthetic routes, hurry up and to see.

Reference£º
Patent; IMMUNOGEN, INC.; US2004/235840; (2004); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials.24621-61-2,A new synthetic method of this compound is introduced below.24621-61-2

To a solution of (S)-1,3-butanediol (807 mg) in DMF (10 mL) at 0C was added potassium t-butoxide (7.2 mL of a 1M solution in THF). After 1 h, the mixture was cooled to -20C and then 2-chloro-3-(4-methylsulfonyl)phenyl-5-trifluoromethylpyridine (1 g) was added as a solid. The resulting mixture was stirred for 24 h, warming to r.t. To the mixture was added saturated NH4Cl and the mixture was extracted with ethyl acetate. The organics were dried (MgSO4) and concentrated. Flash chromatography (1:1 hexane/ethyl acetate) provided the title compound as a white solid (323 mg).1H NMR (300 MHz, acetone-d6): d 1.15 (d, 3H), 1.75-2.00 (m, 2H), 3.15 (s, 3H), 3.65 (d, 1H), 3.85-4.00 (m, 1H), 4.60 (dd, 2H), 7.95 (d, 2H), 8.03 (d, 2H), 8.10 (d, 1H), 8.57 (d, 1H).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, (S)-Butane-1,3-diol.

Reference£º
Patent; MERCK FROSST CANADA & CO.; EP1012142; (2004); B1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

538-58-9,The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a downstream synthesis route of the compound 538-58-9

General procedure: A mixture of divinyl ketone (0.5 mmol), indolin-2-one (0.6 mmol)and cesium carbonate (0.5 mmol) in methylene chloride (5 mL) wasstirred at room temperature for the appropriate time. Then the resultingmixture was extracted with ethyl acetate (2 ¡Á 5 mL). The combinedorganic layers were dried over anhydrous magnesium sulfate andconcentrated under reduced pressure. The residues were isolated bycolumn chromatography using petroleum ether and ethyl acetate (v/v5 : 1) as eluent to give the pure product.2,6-Diphenylspiro[cyclohexane-1,3?-indoline]-2?,4-dione (2a): Whitesolid; m.p. 216-218 C; 1H NMR (600 MHz, CDCl3): delta 8.70 (s, 1H),7.23-7.20 (m, 3H), 7.00-6.95 (m, 6H), 6.90 (d, J = 7.3 Hz, 2H), 6.72 (t,J = 7.6 Hz, 1H), 6.56 (d, J = 7.7 Hz, 1H), 6.21 (d, J = 7.6 Hz, 1H), 3.96(t, J = 14.3 Hz, 1H), 3.80 (dd, J = 14.0, 3.7 Hz, 1H), 3.69 (t, J = 6.0 Hz,1H), 3.62 (dd, J = 16.1, 6.0 Hz, 1H), 2.99 (dd, J = 16.1, 5.9 Hz, 1H),2.72 (dd, J = 15.8, 3.4 Hz, 1H); 13C NMR (150 MHz, CDCl3): delta 211.4,180.9, 140.2, 139.9, 138.0, 130.0, 129.3, 128.2, 128.1, 128.0, 127.9,127.4, 127.2, 125.9, 121.4, 109.3, 56.0, 46.6, 45.5, 42.7, 41.9; Anal.calcd for C25H21NO2: C, 81.72; H, 5.76; N, 3.81; found: C, 81.66; H,5.78; N, 3.80%.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 1,5-Diphenylpenta-1,4-dien-3-one.

Reference£º
Article; Li, Zheng; Li, Jiasheng; Yang, Jingya; Journal of Chemical Research; vol. 41; 3; (2017); p. 168 – 171;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 24621-61-2

To a stirring solution of (S)-1, 3-butanediol (1.0 g, 0.01 MMOL) and triethylamine (1.39 g, 0.014 MMOL) in dichloromethane (10 mL) at-20C was added dropwise p- toluenesulfonyl chloride and the mixture was stirred for 2 h. The reaction mixture was then warmed to RT and stirred overnight. The reaction mixture was poured into cold H20 (20 mL), and extracted three times with DICHLOROMETHANE. The organic extracts were then washed with brine. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to give 2.6 g (96% yield) of title compound as an oil. MS (ESI) 244.8 (M+). The crude tosylat was used without further purification.

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,(S)-Butane-1,3-diol,24621-61-2,its application will become more common.

Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/43939; (2004); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

4254-15-3,Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. (S)-Propane-1,2-diol,4254-15-3, This compound has unique chemical properties. The synthetic route is as follows.

To separate the propylene glycol enantiomers on a chiral gas chromatography column, they were derivatized with acetic anhydride to the methyl esters. Into a small vial equipped with a Teflon lined stir bar was added 1 mL diethyl ether and equal amounts (5-10 drops) propylene glycol, pyridine, and acetic anhydride. The reaction mixture was stirred 3 hours at room temperature, washed with deionized 0 (3 x 1 mL) and dried over Na2S04. The derivatized product was then analyzed via gas chromatography. The diacetate was obtained with an ee of 97percent when (R,i?)-(Cl-salcy)CoN03 was used, and with an ee of 96percent when (5,S)-(Cl-salcy)CoN03 was used, indicating that both enantiomers produced highly regioregular poly(propylene succinate).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 4254-15-3.

Reference£º
Patent; CORNELL UNIVERSITY; COATES, Geoffrey; WHITEHEAD, Julie; (60 pag.)WO2016/25675; (2016); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

538-58-9,A common heterocyclic compound, 538-58-9,1,5-Diphenylpenta-1,4-dien-3-one, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: Method A: A mixture of appropriate derivatives of both 1,3-diaryl-2-propen-1-ones (1.0 equiv.) and aryl hydrazine (1.1 equiv.) was taken in a 100mL round-bottomed flask in 95% ethanol (25mL). Addition of a drop of H2SO4 initiated the precipitation. The reaction mixture was refluxed for 3 to 5h and cooled to room temperature to form precipitate in most of the cases. The residue was filtered, washed with water and dried under vacuum. In some cases where precipitate was not observed after cooling to room temperature, water was added to obtain precipitate.

The chemical industry reduces the impact on the environment during synthesis, 538-58-9,1,5-Diphenylpenta-1,4-dien-3-one,I believe this compound will play a more active role in future production and life.

Reference£º
Article; Ananthnag, Guddekoppa S.; Adhikari, Adithya; Balakrishna, Maravanji S.; Catalysis Communications; vol. 43; (2014); p. 240 – 243;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials.24621-61-2,A new synthetic method of this compound is introduced below.24621-61-2

(S)-(+)-Butane-1 ,3-diol (3.00 mmol, 0.270 g) was added to a stirred solution of imidazole (5.99 mmol, 0.41 g) and tert-butyldimethylsilyl chloride (3.00 mmol, 0.45 g) at room temperature. After six hours at room temperature water (50 mL) was added and extracted twice with dichloromethane (20 mL). The combined organic extracts were washed with brine, dried (sodium sulfate) and concentrated in vacuo to yield (S)-4- (tert-butyldimethylsilyloxy)butan-2-ol (0.654 g).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, (S)-Butane-1,3-diol.

Reference£º
Patent; N.V. ORGANON; MAN de,, Adrianus Petrus Antonius; REWINKEL,, Johannes Bernardus Maria; JANS,, Christiaan Gerardus Johannes Maria; RAAIJMAKERS,, Hans Cornelis Andreas; WIJKMANS,, Jacobus Cornelis Henricus Maria; WO2011/95556; (2011); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate

24621-61-2,A common heterocyclic compound, 24621-61-2,(S)-Butane-1,3-diol, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

(Example 5-1) Under ice cooling, to a dichloromethane solution (20.0 ml) of (S)-1,3-butanediol (519 mg) were added triethylamine (1.04 ml) and tert-butylchlorodiphenylsilane (1.63 ml), followed by stirring at room temperature overnight. The reaction solution was poured into a saturated aqueous ammonium chloride solution, and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography to afford (2S)-4-{[tert-butyl(diphenyl)silyl]oxy}butan-2-ol (1.69 g). 1H NMR(400 MHz,CDCl3) delta: 1.05 (9H, s), 1.22 (3H, d, J = 6.3 Hz), 1.58-1.68 (1H, m), 1.69-1.81 (1H, m), 3.31 (1H, d, J = 2.0 Hz), 3.80-3.91 (2H, m), 4.07-4.15 (1H, m), 7.37-7.50 (6H, m), 7.69 (4H, d, J = 6.2 Hz).

The chemical industry reduces the impact on the environment during synthesis, 24621-61-2,(S)-Butane-1,3-diol,I believe this compound will play a more active role in future production and life.

Reference£º
Patent; Daiichi Sankyo Company, Limited; EP2471792; (2012); A1;,
Synthesis and Crystal Structure of a Chiral?C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis
Chiral lanthanide(III) complexes of sulphur¨Cnitrogen¨Coxygen ligand derived from aminothiourea and sodium?D-camphor-¦Â-sulfonate