Hydrochloric Acid → N-Palmitoylglycine

Participants

Reaction Steps

First, 27.3 g (364 mmol) of glycine and 29.1 g (727 mmol) of sodium hydroxide were dissolved in a mixed solvent of 450 g composed of i-propanol and 200 g of water under stirring at room temperature, then cooled to 10° C. Next, 100 g (364 mmol) of palmitic acid chloride was added dropwise thereto over a period of 1 hour. The reaction product was returned to room temperature, then stirred for about 15 hours. Next, 400 g of water was added thereto, following which 73.8 g (727 mmol) of 35% hydrochloric acid was added dropwise. The solid that deposited out was recovered, slurry washed, and purified by re-crystallization from methanol, giving 36.4 g (yield, 32%) of N-palmitoyl-Gly as a white solid.

Provenance & Evidence