With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.128453-98-5,4-(tert-Butoxycarbonyl)thiomorpholine-3-carboxylic acid,as a common compound, the synthetic route is as follows.,128453-98-5
o a solution of N-Boc thiomorpholine carboxylic acid (0.803 g, 2.96 mmol) in 16 mL of anhydrous dichloromethane was added O-benzotriazol-1-yl-Lambda/,Lambda/,Lambda/’,Lambda/’-tetramethyluronium tetrafluoroborate (TBTU) (1.03 g, 3.22 mmol) and the solution was stirred for 45 min. A solution of D-serine methyl ester hydrochloride (0.911 g, 5.85 mmol) and Huenig’s base (1.02 mL, 5.85 mmol) in dichloromethane was prepared and added to the reaction mixture. The reaction was left stirring at room temperature overnight. UPLC-MS analysis showed conversion to the product. The reaction was diluted with dichloromethane and extracted with water, dried (Na2SO4), and the solvent was removed. The crude (1.73 g) was taken to the next step without further purification; To a solution of N-Boc thiomorpholine carboxylic acid (0.488 g, 1.97 mmol) and O- benzotriazol-1-yl-Lambda/,Lambda/,Lambda/’,Lambda/’-tetramethyluronium tetrafluoroborate (TBTU) (0.697 g, 2.17 mmol) in 5 mL of anhydrous dichloromethane was added DIPEA (0.7 mL, 3.95 mmol) and the solution was stirred for 30 mins. To a suspension of D-serine methyl ester hydrochloride (0.47 g, 3.95 mmol) in 5 mL of anhydrous dichloromethane was added DIPEA (0.7 mL, 3.95 mmol) and the resulting solution was stirred for 30 mins. Then the solution containing the serine free base was added to the reaction mixture and it was left stirring at room temperature overnight.Water was added to the reaction mixture and the two phases were separated. The aqueous layer was extracted with dichloromethane (3X) and the combined organic phases were dried (Na2SO4) and evaporated to dryness. This crude material (1.66 g) was used in the next step without further purification. UPLC-MS: m/z= 349 (M+1 ) (at) t=0.59 min
The synthetic route of 128453-98-5 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/28654; (2007); A1;,
Thiomorpholine – Wikipedia
Thiomorpholine | C4H9NS – PubChem