Trifluoroacetic acid → HCID 9847163, compound

Participants

Reaction Conditions

Reaction Steps

TBTU (0,72 g) was added portionwise to a stirred solution of N-methylmorpholine (0.5 mL) and O-tert-butylhydroxylamine hydrochloride (0.43 g) and 3-[(4′-chloro[1,1′-biphenyl]-4-yl)sulfonyl]-2-[(phenylsulfanyl)methyl]-propanoic acid (0.5 g) in 20 mL of DMF and 20 mL of acetonitrile cooled at −5° C. After stirring at ambient temperature overnight, the resulting solution was diluted with ethyl acetate and sequentially washed with 0.1 M citric acid and 0.1 M NaHCO3. After drying over anhydrous sodium sulfate and removal of the solvent, the crude reaction mixture was treated with trifluoroacetic acid (10 mL) and kept aside for 6 hours. The solvent was removed and the residue was partitioned between ethyl acetate and 0.1 M NaHCO3. After drying, the solvent was evaporated off and the residue was chromatographed on silica gel eluting with chloroform/cyclohexane 2/3 to afford, after crystallization from ethyl acetate, 0.35 g of the title compound, mp . . .

Provenance & Evidence