Triethylamine → N-[(1R,2Z)-2-amino-2-hydroxyimino-1-phenylethyl]-3-(4-phenylphenyl)sulfonyl-1,3-thiazolidine-2-carboxamide

Participants

Reaction Steps

Triethylamine (92 μl, 0.66 mmol) was slowly added to a suspension of product Ic, e.g., 3-(biphenyl-4-ylsulfonyl)-N-[cyano(phenyl)methyl]-1,3-thiazolidine-2-carboxamide, and hydroxylamine.hydrochloride (46 mg, 0.66 mmol) in ethanol (5 mL), under stirring. The reaction mixture was heated under reflux for 16 h, and then cooled to RT. The solvents were removed and the resulting solid was suspended in water and extracted with three portions of EtOAc. Combined organic phases were dried over MgSO4, filtrated and evaporated, affording intermediate Id, e.g., N-[(1R,2Z)-2-amino-2-(hydroxyimino)-1-phenylethyl]-3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide (272 mg, quantitative yield) which was directly used in the next step.

Provenance & Evidence