tert-butyl (2RS,4SR,5RS)-1-{2-[3-(3-(benzyloxycarbonyl)phenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-(phenylsulphonyl)pyrrolidine-2-carboxylate → (2S,4R,5R)-3-{3-[2-(4-benzyl-2-tert-butoxycarbonyl-5-phenyl-1-pyrrolidinyl)-2-oxoethyl]ureido}benzoic acid

Participants

Reaction Steps

A The reaction is carried out in a way analogous to that described in Example 2A, but from 5.8 g of tert-butyl (2RS,4SR,5RS)-1-{2-[3-(3-(benzyloxycarbonyl)phenyl)ureido]acetyl}-5-(2-fluorophenyl)-4-(phenylsulphonyl)pyrrolidine-2-carboxylate and 0.6 g of 10% palladium-on-charcoal in 200 cm3 of ethanol. After treatment, there are obtained 2.85 g of (2RS,4SR,5RS)-3-{3-[2-(2-tert-butoxycarbonyl-5-(2-fluorophenyl)-4-phenylsulphonyl-1-pyrrolidinyl)2-oxoethyl]ureido}benzoic acid [Rf =0.25; eluent: methylene chloride/methanol (90/10)].

Provenance & Evidence