Crystallization Induced Asymmetric Transformation: Synthesis of D-p-Hydroxyphenylglycine
- 1 September 1994
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 24 (17), 2449-2459
- https://doi.org/10.1080/00397919408010553
Abstract
D-p-hydroxyphenylglycine (D-HPG) is prepared from racemic HPG via salicylaldehyde mediated resolution-racemization of the corresponding D-3-bromocamphor-8-sulfonate salt in acetic acid. After slurry purification to improve the de to >99.9%, the crystallized salt is neutralized to produce D-HPG in 92% overall yield and 99.9% ee.Keywords
This publication has 9 references indexed in Scilit:
- Silafunctional compounds in organic synthesis. 33. Metalated allylaminosilane: a new, practical reagent for the stereoselective .alpha.-hydroxyallylation of aldehydes to erythro-1,2-diol skeletonsThe Journal of Organic Chemistry, 1987
- Asymmetric Transformation of Dl-p-Hydroxyphenylglycine by a Combination of Preferential Crystallization and Simultaneous Racemization of the o-ToluenesulfonateBulletin of the Chemical Society of Japan, 1985
- Racemization of Optically Active Amino Acid Salts and an Approach to Asymmetric Transformation of Dl-Amino AcidsBulletin of the Chemical Society of Japan, 1983
- Method for the racemization of optically active amino acidsThe Journal of Organic Chemistry, 1983
- The Stability of the Supersaturation State in Optical Resolution by the Preferential Crystallization ProcedureBulletin of the Chemical Society of Japan, 1981
- Microbial transformation of hydantoins to amino acids. Part V. Synthesis of N-carbamyl-D-2-thienyl-glycine and D-2-thienylglycine by microbial hydantoinase.Agricultural and Biological Chemistry, 1980
- Preparation of D-p-hydroxyphenylglycine. Optical resolution of DL-p-hydroxyphenylglycine with d-3-bromocamphor-8-sulfonic acid.Agricultural and Biological Chemistry, 1979
- Preparation of D-p-hydroxyphenylglycine: Optical resolution of DL-p-hydroxyphenylglycine by preferential crystallization procedure.Agricultural and Biological Chemistry, 1978
- Derivatives of 6-aminopenicillanic acid. Part XI. α-Amino-p-hydroxy-benzylpenicillinJournal of the Chemical Society C: Organic, 1971