Dimethyl Sulfoxide → HCID 86585077, compound

Participants

Reaction Steps

140 mg (0.26 mmol) (2S,4R)-[4-(4-methoxy-benzylsulfanyl)-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanone in 2 ml TFA were treated with 0.45 ml (6 mmol) trimethylsilyl chloride and 0.3 ml (6 mmol) DMSO for 2 h at RT, added to a sat. solution of Na2CO3 and extracted with EtOAc, washed with brine and dried. The crude product was dissolved in 6 ml acetonitrile, a sat. solution of K2CO3 in MeOH and 100 mg (0.65 mmol) DTT were added. The solution was stirred at RT for 1.5 h, the solution was acidified with 1M aq KHSO4 and the inorganic phase was extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4, filtered and evaporated. Flash chromatography yielded 89.5 mg (81%) (2S,4R)-[4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidin-2-yl]-(4-methoxy-phenyl)-methanone as light yellow solid, MS: 292 (M-C5H9O)+, 135 (C5H9O)+.

Provenance & Evidence