tert-Butanol → 7-[3-Hydroxy-4-(1,1,4-trioxo-1,2,5-thiadiazolidin-2-yl)-benzyl]-azepan-2-one

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Reaction Steps

To a cooled solution of chlorosulfonyl isocyanate (315 mg, 2.22 mmol) in CH2Cl2 (8 mL) is added dropwise a solution of t-butanol (165 mg, 2.22 mmol) in CH2Cl2 (1 mL). The solution is stirred at RT for 45 min and re-cooled, then a solution of [2-benzyloxy-4-(7-oxo-azepan-2-ylmethyl)-phenylamino]-acetic acid methyl ester (600 mg, 1.48 mmol) and triethylamine (252 mg, 2.52 mmol) in CH2Cl2 (2 mL) is added dropwise. The mixture is stirred at RT for 3 h then washed with water. The organic phase is dried over Na2SO4 and the solvent is removed under reduced pressure. The residual oil is purified by flash chromatography using EtOAc/CH2Cl2 (1:1) as eluent to give the title compound.

Provenance & Evidence