Pyridine → 3-Biphenyl-4-yl-2-[5-bromo-2-(4-tert-butyl-benzenesulfonylamino)-benzoylamino]-propionic acid methyl ester

Participants

Reaction Steps

To a stirring solution of (2S)-(2-amino-5-bromo-benzoyl-amino)-3-biphenyl-4-yl-propionic acid methyl ester (1.0 g, 2 mmol) prepared above dissolved in DCM containing pyridine (1.58 g, 4 mmol), was added 4-tert-butylbenzenesulfonyl chloride (1.20 g, 2.5 mmol) at 0° C. The reaction mixture was stirred at rt for 3 h, extracted with DCM, washed with 1M HCl and brine, and was concentrated in vacuo, followed by column chromatography purification (silica, CH2Cl2) giving 3-biphenyl-4-yl-2-[5-bromo-2-(4-tert-butyl-benzenesulfonylamino)-benzoylamino]-propionic acid methyl ester (1.25 g) as a white solid which was hydrolyzed according to Procedure C yielding the title compound (1.23 g) as a white solid.

Provenance & Evidence