Sarcosine → N-Carbobenzoxysarcosine

Participants

Reaction Steps

This material was prepared following the method of R. S. Tipton and B. A. Pawson [J. Org. Chem., 26, 4648 (1961)]. Sarcosine (8.90 g, 1.0 mole) was dissolved in 500 ml of 2 N sodium hydroxide with cooling in an ice bath. Simultaneously, 550 ml of 2 N sodium hydroxide and benzyl chloroformate [196 g (95%), 1.095 moles] were added over a period of one hour with rapid stirring. The resulting reaction mixture was stirred for about 18 hours at ambient temperature, after which time it was extracted with three 250 ml portions of diethyl ether. Ethyl acetate (500 ml) was then added to the aqueous phase, followed by the careful addition of 200 ml of concentrated hydrochloric acid. The organic layer was separated, washed with two 500 ml portions of water followed by 300 ml of saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. Evaporation of the solvent under reduced pressure after removal of the drying agent by filtration gave 213 g (95%) of N-phenylmethoxycarbonyl-sarcosine as an oil which was identified by nmr spectroscope and used without further purification.

Provenance & Evidence