6-Aminohexanoic Acid → 6-(((Phenylmethoxy)carbonyl)amino)hexanoic acid

Participants

Reaction Steps

To a solution of 6.56 g (50 mmoles) of 6-aminohexanoic acid in 25 ml of 2N aqueous sodium hydroxide solution was added 5 ml of ethyl ether. To the mixture, while being cooled in ice and stirred, were added dropwise over a period of 30 minutes 10 ml of benzyloxycarbonyl chloride and 37.5 ml of 2N aqueous sodium hydroxide solution. After the addition, the temperature was brought back to room temperature and the stirring was continued for 2 hours. The reaction mixture was washed twice with 20 ml of ethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid and extracted 3 times with 50 ml of ethyl acetate. The extract solutions were combined, washed with saturated saline, dried over anhydrous sodium sulfate and freed from the solvent by distillation to obtain 12.16 g (92% yield) of 6-benzyloxycarbonylaminohexanoic acid with a melting point of 127°-128° C.

Provenance & Evidence