Potassium Carbonate → HCID 86585065, compound

Participants

Reaction Steps

To 200 mg (0.52 mmol) (2S,4R)-4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carboxylic acid in 10 ml toluene and 4 ml THF were added 226 μl (2.6 mmol, 5eq) oxalyl chloride and the solution was stirred at RT for 2 h, and was concentrated. The residue was dissolved in 8 ml THF, and the solution was added at 0° C. to a suspension of 180 mg (1.19 mmol, 2.2 eq) 4-methylamino benzoic acid and 360 mg (2.6 mmol, 5eq) K2CO3 in 8 ml THF. After 2.5 h the solution was acidified by 1M KHSO4 and extracted with EtOAc, the organic phase was washed with brine and dried over Na2SO4. Column chromatography yielded 91 mg (35%) (2S,4R)-4-[[4-Acetylsulfanyl-1-(naphthalene-2-sulfonyl)-pyrrolidine-2-carbonyl]-methyl-amino]-benzoic acid as white solid, MS: 513 (MH+).

Provenance & Evidence