4-Chlorobenzoic Acid → 2-{4-[4-(4-Chloro-benzoylamino)-phenyl]-thiazol-2-ylcarbamoyl}-pyrrolidine-1-carboxylic acid benzyl ester

Participants

Reaction Steps

A mixture of 4-Chlorobenzoic acid (0.017 g, 0.11 mmol), HATU (0.042 g, 0.11 mmol), and DIEA 0.09 mL, 0.67 mmol) in DMF (2 mL) was stirred at room temperature for 1 h. (S)-2-[4-(4-Amino-phenyl)-thiazol-2-ylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (FW=422.5096 , 0.029 g, 0.054 mmol) was added. The reaction mixture was stirred at room temperature for 20 h. The mixture was filtered to afford the crude product. The mixture was filtered and separated by reverse phase HPLC (20-100% of buffer B; buffer A: water containing 0.1% TFA; buffer B: MeCN containing 0.1 TFA). The combined fraction was evaporated to dryness to furnish the desired product. MS: 562.1(M+H+).

Provenance & Evidence