p-Bromobenzenesulfonyl chloride → tert-Butyl {2-[(4-bromobenzene-1-sulfonyl)amino]ethyl}carbamate

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Reaction Steps

4-Bromobenzenesulfonyl chloride (256 mg, 1 mmol) was added dropwise to a solution of 1,1-dimethylethyl (2-aminoethyl)carbamate (197 mg, 1 mmol) and triethylamine (0.42 mL, 3 mmol) in CH2Cl2 (5 mL) at ambient temperature. The mixture was stirred at ambient temperature overnight. The mixture was then concentrated, and the crude product was purified by chromatography on a silica gel column using 0 to 5% MeOH/CH2Cl2 to give 362 mg (96%) of 1,1-dimethylethyl (2-{[(4-bromophenyl)sulfonyl]amino}ethyl)carbamate as a white solid. 1H NMR (400 MHz, CDCl3): δ 7.75-7.68 (m, 2H), 7.67-7.61 (m, 2H), 5.28 (bs, 1H), 4.78 (bs, 1H), 3.26-3.20 (m, 2H), 3.11-3.03 (m, 2H), 1.43 (s, 9H); LRMS (ESI), m/z 379/381 (M+H).

Provenance & Evidence