Large-Scale Preparation of (S)-α-Methylmethionine from the Parent Amino Acid

Authors

  • Albert K. Beck Laboratorium für Organische Chemie Eidgenössische Technische Hochschule Zürich ETH-Zentrum, Universitätstrasse 16 CH 8092 Zürich
  • Dieter Seebach Laboratorium für Organische Chemie Eidgenössische Technische Hochschule Zürich ETH-Zentrum, Universitätstrasse 16 CH 8092 Zürich

DOI:

https://doi.org/10.2533/chimia.1988.142

Abstract

The sodium salt of methionine is treated with pivalaldehyde to give an imine which is cyclized to an 1,3-oxazolidin-5-one by treatment with benzoyl chloride. The 2,4-cis-substituted heterocycle (6) is isolated by crystallization, methylated through the Li-enolate, and hydrolyzed to give the title compound with overall retention of configuration (ca. 10 g of title compound from 45 g of methionine).

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Published

1988-04-30

Issue

Vol. 42 No. 4 (1988): Forschung/Research

Section

Articles

License

Copyright (c) 1988 Albert K. Beck

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
A. K. Beck, D. Seebach, Chimia 1988, 42, 142, DOI: 10.2533/chimia.1988.142.