Triethylamine → [2-(1-Chloro-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert-butyl ester

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Reaction Steps

Powdered 1-chloro-isoquinoline-5-sulfonyl chloride (10.0 g, 38.2 mmol) is added in portions to a stirred solution of (2-amino-ethyl)-carbamic acid tert-butyl ester (7.33 g, 45.8 mmol) and NEt3 (10.7 mL, 76.4 mmol) in anhydrous CH2Cl2 (200 mL) at 0° C. under nitrogen. The resultant mixture is allowed to stir at ambient temperature for 4 hours. The mixture is concentrated and chromatographed on silica gel (gradient 0-5% CH3OH in CH2Cl2) to give 13.8 g (35.8 mmol, 94% yield) of the title compound as foam. ESIMS: m/z 386 [(M+H)+, 35Cl], 388 [(M+H)+, 37Cl]. Analysis for C16H20ClN3O4S: calcd: C, 49.80; H, 5.22; N, 10.89; found: C, 49.70; H, 5.22; N, 10.72.

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