A Useful Synthetic Method of dl-Threonine Using α-Isocyanoacetamides
- 1 August 1978
- journal article
- research article
- Published by Oxford University Press (OUP) in Agricultural and Biological Chemistry
- Vol. 42 (8) , 1565-1569
- https://doi.org/10.1080/00021369.1978.10863205
Abstract
A reaction of .alpha.-isocyanoacetic acid amides with acetaldehyde provided a useful method for the synthesis of threonine. The reaction in the presence of KOH in methanol afforded predominantly trans-5-methyl-4-N''-substituted-aminocarbonyl-2-oxazoline, which was easily hydrolyzed to DL-threonine in a high yield. This method was extended to the synthesis of threo-.beta.-hydroxynorvaline and threo-.beta.-hydroxyleucine in excellent yields.This publication has 7 references indexed in Scilit:
- Alkylation of α-Isocyanoacetamides; Synthesis of 1,4,4-Trisubstituted 5-Oxo-4,5-dihydroimidazoles1Synthesis, 1977
- Synthesis of amino acids and related compounds. 7. Convenient synthesis of 3-substituted pyrrole-2,4-dicarboxylic acid estersThe Journal of Organic Chemistry, 1974
- Synthesen mit α‐metallierten Isocyaniden, XV1) 4‐Äthoxycarbonyl‐2‐oxazoline und ihre Hydrolyse zu N‐Formyl‐β‐hydroxy‐α‐aminosäureäthylesternEuropean Journal of Organic Chemistry, 1972
- Formation of β-Hydroxyleucine from β-Ispropylglycidic AcidNippon kagaku zassi, 1971
- α-Aminoisobutyric Acid, β-Hydroxyleucine, and γ-Methylproline from the Hydrolysis of a Natural ProductNature, 1958
- Stereochemistry of the β-Phenylserines: Improved Preparation of Allophenylserine1Journal of the American Chemical Society, 1953