Phenol → HCID 86585048, compound

Participants

Reaction Steps

157 mg (0.24 mmol) (2S,4R)-4-(2-{[4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino}-acetylamino)-benzoic acid ethyl ester were treated with 0.1 M LiOH according to 5.2., the crude product (2S,4R)-4-(2-{[4-(4-Methoxy-benzylsulfanyl)-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino}-acetylamino)-benzoic acid was dissolved in 1 ml TFA and heated to 75° C. in the presence of 23 mg (0.24 mmol) phenol for 1.5 h. The solvent was evaporated, the oil dissolved in toluene and evaporated (twice), the residue was titurated from hexane to yield 45 mg (2S,4R)-4-[2-[[4-Mercapto-1-(2-phenyl-ethanesulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino]-acetylamino]-benzoic acid as light yellow solid, MS: 506 (MH+).

Provenance & Evidence