Water → tert-Butyl N-(2-((methylsulfonyl)oxy)ethyl)carbamate

Participants

Reaction Steps

To a solution of Boc-glycinol (25.0 g, 155 mmol) and N,N-diisopropylethylamine (32.4 mL, 186 mmol) in anhydrous dichloromethane (70 mL) was added methanesulfonyl chloride (19.5 mL, 171 mmol) dropwise under ice-water cooling. The mixture was stirred at room temperature for 2 hours. Water was added to the mixture, and the product was extracted with CH2Cl2. The organic layer was dried over Na2SO4, and the solvent was removed in vacuo to give methanesulfonic acid 2-(tert-butoxycarbonylamino)ethyl ester as a crude oil (37 g, 99.7% yield) which was used for the next step without further purification.

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