Hydroxyamine hydrochloride → HCID 88162749, compound

Participants

Reaction Steps

0.5 g of hydroxylamine hydrochloride in solution in 6 cm3 of water is added to a solution of 3 g of tert-butyl (2RS,5SR)-1-{2-[3-(3-acetylphenyl)ureido]acetyl}-5-phenylprolinate in 12 cm3 of methanol and 6 cm3 of pyridine. The reaction mixture is heated under reflux for 2 hours. After evaporation of the solvents under reduced pressure at a temperature in the vicinity of 45° C., the residue is taken up in 100 cm3 of ethyl acetate and the organic phase is washed with 3 times 50 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure. The crude product obtained is purified by chromatography on silica [eluent: dichloromethane/methanol (95/5 by volume)]. The fractions containing the expected product are combined and concentrated to dryness under reduced pressure at a temperature in the vicinity of 40° C. After recrystallization in acetonitrile, 1.1 g of tert-butyl (E)-(2RS,5SR)-1-{2-{3-[3-(1-hydroxyiminoethyl)phenyl]ureido}acetyl}-5-phenylprolinate, melting at 118° C., are obtained.

Provenance & Evidence