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

Participants

Reaction Steps

A solution of 6-aminocaproic acid (13.1 g, 0.10 mole) in 2.5 N NaOH (40 ml, 0.10 mole) was cooled to 0° and benzyloxycarbonyl chloride (18.7 g, 0.11 mole) in ether (25 ml and 2.5N NaOH (50 ml, 0.125 mole) were added simultaneously in several portions, with vigorous stirring, over a 1 hr period. The reaction mixture was extracted with ether (3 × 50 ml), cooled in an ice-bath and acidified with 6M HCl. The crystalline product was recrystallized from ether-pet ether to give 19.4 g of product (73.2%); mp 54°-55.5°.

Provenance & Evidence