N-Methylbenzylamine → HCID 86585061, compound

Participants

Reaction Steps

To 300 mg (0.44 mmol) (2S,4R)-4-[(3R,5S)-5-Carboxy-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid in 25 ml CH2Cl2 were added 100 μl (0.89 mmol, 1 eq) 4-methyl morpholine, followed by 331 mg (1.1 mmol, 1.25 eq) TPTU and 115 μl (0.89 mmol, 1 eq) N-methylbenzyl amine. The solution was stirred at RT over night. The mixture was added to a 1M KHSO4 solution, extracted with EtOAc and the organic phase was washed with 5% aq. NaHCO3 solution and brine. The solution was dried over Na2SO4, filtered and evaporated, yielding 313 mg (81%) (2S,4R)-4-[(3R,5S)-5-(Benzyl-methyl-carbamoyl)-1-(naphthalene-2-sulfonyl)-pyrrolidin-3-yldisulfanyl]-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl-methyl-amide as colorless foam, which was subjected to disulfide cleavage according to general procedure 4.1. to give (2S,4R)-4-Mercapto-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid benzyl-methyl-amide as white solid, MS: 441 (MH+).

Provenance & Evidence