Sodium Methoxide → HCID 86585064, compound

Participants

Reaction Steps

80 mg (0.134 mmol) (2S,4R)-4-[[[[4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-amino]-acetyl]-methyl-amino]-benzoic acid methyl ester in 5 ml methanol were treated with 335 μl 0.6M (0.2 mmol) sodium methanolate in methanol at 0° C. for 1 h. The solution was poured on EtOAc/1M KHSO4 and the inorganic phase was extracted with EtOAc, the organic phases were washed with brine, dried over Na2SO4 and were evaporated. Column chromatography with EtOAc yielded 70 mg (quant) (2S,4R)-4-[[[[4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino]-acetyl]-methyl-amino]-benzoic acid methyl ester as white foam, MS: 556 (MH+).

Provenance & Evidence