Potassium ethanethioate → HCID 86585044, compound

Participants

Reaction Conditions

Reaction Steps

5.42 g (11 mmol) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-(toluene-4-sulfonyloxy)-pyrrolidine-2-carboxylic acid methyl ester were suspended in 60 ml DMF and treated with 1.89 g (16.55 mmol, 1.5 eq) potassium thioacetate. The reaction mixture was heated to 100° C. for 45 min, cooled to RT and concentrated. The residue was redissolved in CH2Cl2/sat. NaHCO3 solution. The inorganic phase was extracted with EtOAc, the organic phases were washed with brine and dried over Na2SO4. After evaporation the residue was purified by column chromatography yielding 3.6 g (83%) (2S,4S)-4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester as orange oil, MS: 394 (MH+).

Provenance & Evidence