Synthesis Of Chiral α-amino Amide

Chiral a-amino amide is a important intermediate in organic synthesis due to it’s high hydrophilic. It plays a great role in the preparations of plastics, lubricants, detergents, and it can be used as chiral unit in asymmetric synthesis.The title product was prepared with aliphatic aldehyde as raw material by cyanohydrin reaction, ammonolysis, hydrolysis and resoluion. The catalysts of hydrolysis were strong alkali and carbonyl compounds. In order to obtain chiral a-amino amide, we conducted chemical resolution with L-tartaric acid as resolution agent and the mother liquor of resolution was racemizated through high temperature and strong alkali.In this paper, the synthetic route was definited and modified by preparing (S)-a-aminobutanamide hydrochloride as an example. On the sufficient understanding to mechanism of alkaline hydrolysis, the possible factors that influence the side reactions were discussed. And the idea of asymmetric conversion was introduced to the enantiomeric separation which greatly improve the resolution yield. The mother liquor of resolution was racemized with high temperature and could again serve as the raw material of resolution.This route shows great industrial value since it is environmentally friendly, low-cost and user-friendly. Furthermore it provides a important intermediate for the synthesis of other compounds.