Triethylamine → Methanesulfonic acid 2-tert-butoxycarbonylamino-2-methyl-propyl ester

Participants

Reaction Conditions

Reaction Steps

Dichloromethane (50 mL) and triethylamine (9.72 ml, 69.7 mmol) were added to a flask containing tert-butyl (1-hydroxy-2-methylpropan-2-yl)carbamate (3.30 g, 17.4 mmol). The reaction mixture was stirred and then chilled to 0° C. for 10 minutes. Methanesulfonyl chloride (2.72 ml, 34.9 mmol) was dissolved in dichloromethane (15 mL) and slowly added to the reaction mixture, which was then allowed to stir at 0° C. for 2 hours. The reaction was quenched with saturated aqueous sodium bicarbonate solution and the organic layer was separated. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to afford 2-((tert-butoxycarbonyl)amino)-2-methylpropyl methanesulfonate. 1H NMR (500 MHz, DMSO-d6): δ 6.73 (s, 1H), 4.20 (s, 2H), 3.12 (s, 3H), 1.36 (s, 9H), 1.17 (s, 6H).

Provenance & Evidence