A synthesis of dl-α-aminoadipic acid and its N-chloroacetyl derivative

✍ Scribed by Thomas G. Wood; Richard A. Hartline

• Publisher: Elsevier Science
• Year: 1971
• Tongue: English
• Weight: 319 KB
• Volume: 43
• Category: Article
• ISSN: 0003-2697
• DOI: 10.1016/0003-2697(71)90135-7

✦ Synopsis

During an investigation

of the bacterial degradation of m-a-aminoadipate it became necessary to rapidly synthesize, with ease, large quantities of this compound and to resolve the racemic mixture. Of the available methods of synthesis (1) that of Waalkes et al. ( 2), by amination of diethyl cy-bromoadipate, was the least complex and provided the best yield. However, the amination step by reacting, under pressure, anhydrous ammonia with diethyl cY-bromoadipate required 6 days. A shortened modification of that method was outlined by Rothstein and Greenberg (3). Although the general concept of the modification was sound, these workers did not report details necessary for a successful problem-free synthesis.

Resolution of DL-a-aminoadipic acid can be accomplished by selective enzymic cleavage of N-chloroacetyl+cu-aminoadipic acid with renal acylase I. In numerous attempts to synthesize the N-chloroacetyl derivative of a-aminoadipic acid by the method of Greenstein et al. ( 4) the best yield obtained was 6.5%.

The purpose of this paper is to provide, in detail, the modified a-aminoadipic acid synthesis of Rothstein and Greenberg (3) and to describe modifications necessary for a consistently successful synthesis of N-chloroacetyl-m-a-aminoadipic acid in good yield (Scheme I).

MATERIALS

Monoethyl adipic acid was obtained from Eastman Organic Chemicals, Rochester, New York, chloroacetyl chloride from J. T. Baker Co., Phillipsburg, New Jersey, and ninhydrin from Fisher Scientific Co., Fair Lawn, New Jersey. All other chemicals used were of reagent grade.

l Taken from a portion of the M.S. Thesis,