Benzenesulfonyl chloride → (S)-2-Benzenesulfonylamino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic Acid Tert-butyl Ester

Participants

Reaction Steps

To a solution of (S)-2-amino-3-{3-benzyloxy-4-[1,1,4-trioxo-5-(2-trimethylsilanylethyl)-1,2,5-thiadiazolidin-2-yl]-phenyl}-propionic acid tert-butyl ester (Example 132, step C) (10 mg, 0.249 mmol) and triethylamine (51 mg, 0.5 mmol) in MeCN (5 mL) is added benzenesulfonyl chloride (44 mg, 0.249 mmol) and the mixture is stirred at RT for 2 h. The solvent is removed under reduced pressure and the residue partitioned between methylene chloride and 1N HCl. The organic phase dried over sodium sulfate and the solvent removed under reduced pressure. The residue is purified by flash chromatography using a gradient of 0-40% EtOAc/hexane as eluent to give the title compound: (M−1)−=700.

Provenance & Evidence