2-[(2-chloroacetyl)-methylamino]acetic acid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.8 Grams (0.1 mole) of sarcosine was suspended in 100 ml of ethyl acetate and refluxed under anhydrous conditions with 22.6 grams (0.2 mole) of chloroacetyl chloride for 12 hours. The unreacted sarcosine was then filtered and the excess solvent and chloroacetyl chloride removed from the filtrate by vacuum distillation. The resulting oil was crystallized with the aid of a small quantity of diethyl ether. There was obtained 12.5g (76%) of N-(Chloroacetyl)sarosine whose structure was consistent with infrared analysis and element analysis for C, H, N, and Cl. The unreacted sarcosine was then filtered the excess solvent and chloroacetyl chloride removed from the filtrate by vacuum distillation The resulting oil was crystallized with the aid of a small quantity of diethyl ether There was obtained 12.5g (76%) of N-(Chloroacetyl)sarosine whose structure

Conditions: temp:-5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sarcosine (32.38 g, 363 mmol) was dissolved in 90 mL 4N aqueous sodium hydroxide, and cooled in an ice-salt bath to -5° C. The mixture was stirred vigorously and treated simultaneously with chloroacetyl chloride (32 mL, 402 mmol) and 110 mL 4N aqueous sodium hydroxide dropwise over 20 minutes. After warming to ambient temperature and stirring for 34 hours, the solution was carefully acidified to pH 2 (concentrated hydrochloric acid), saturated with sodium chloride, and extracted with ethyl acetate (2×400 mL). The extracts were combined, dried over anhydrous magnesium sulfate and evaporated to afford N-chloroacetylsarcosine as an oil, sufficiently pure for the next step (39.34 g, 238 mmol, 65%). After warming to ambient temperature stirring for 34 hours extracted with ethyl acetate (2×400 mL) dried over anhydrous magnesium sulfate evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 8.8 Grams (0.1 mole) of sarcosine was suspended in 100 ml of ethyl acetate and refluxed under anhydrous conditions with 22.6 grams (0.2 mole) of chloroacetyl chloride for 12 hours. The unreacted sarcosine was then filtered and the excess solvent and chloroacetyl chloride removed from the filtrate by vacuum distillation. The resulting oil was crystallized with the aid of a small quantity of diethyl ether. There was obtained 12.5g (76%) of N-(Chloroacetyl)sarosine whose structure was consistent with infrared analysis and element analysis for C, H, N, and Cl. The unreacted sarcosine was then filtered the excess solvent and chloroacetyl chloride removed from the filtrate by vacuum distillation The resulting oil was crystallized with the aid of a small quantity of diethyl ether There was obtained 12.5g (76%) of N-(Chloroacetyl)sarosine whose structure