Thioglycolic Acid → HCID 67350930, compound

Participants

Reaction Conditions

Reaction Steps

N-[3-(4-Methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)phenyl]-2-nitrobenzenesulfoneamide (2.50 g, 6.64 mmol) obtained in Step 4 was dissolved in toluene (13 mL), and the mixture was stirred at 60° C. for 5 hours after adding commercially available (S)-(−)-1-tert-butoxycarbonyl-2-pyrrolidinemethanol (2.67 g, 13.3 mmol), diethyl azodicarboxylate (40% toluene solution, 6.1 mL, 13.3 mmol), and triphenylphosphine (3.49 g, 13.3 mmol). Water and ethyl acetate were added to the mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain a crude purified product. The crude purified product was dissolved in DMF (33 mL), and the mixture was stirred for 3 hours after adding DBU (3.98 mL, 26.7 mmol) and mercaptoacetic acid (0.92 mL, 13.3 mmol). Water and ethyl acetate were added to the mixture to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was then purified by silica gel column chromatography to give (S)-1-tert-butoxycarbonyl-2-{N-[3-(4-methyl-5-oxo-4,5-dihydro-1,3,4-oxadiazol-2-yl)phenyl]aminomethyl}pyrrolidine (1.37 g, 55%).

Provenance & Evidence