Sarcosine → N-Carbobenzoxysarcosine

Participants

Reaction Conditions

Reaction Steps

26.7 g (0.3 mol) of sarcosine were dissolved in 150 m (0.3 mol) of 2-N sodium hydroxide. The resulting solution was stirred at 0° C. while 75 ml of 4-N sodium hydroxide and 51.3 ml (ca 360 mmol) of benzyl chloroformate were added alternately and portionwise over a period of 0.5 hour, the temperature being held below 5° C. The mixture was stirred for a further 1 hour while the temperature was allowed to rise to room temperature. The mixture was then extracted with two 300 ml portions of diethyl ether. The aqueous layer was separated, cooled to 0° C. and, while stirring, made acid to Congo red with ca 25 ml of concentrated hydrochloric acid. The mixture was stirred for 1 hour while allowing the temperature to rise to room temperature. The mixture was then extracted with three 300 ml portions of diethyl ether, the combined extracts were dried over sodium sulphate and evaporated to give ca 64 g of N-benzyloxycarbonyl-sarcosine in the form of an oil.

Provenance & Evidence