Title:
GREEN PREPARATION METHOD FOR N-SUBSTITUTED-L-PYROGLUTAMIC ACID ESTER
Document Type and Number:
WIPO Patent Application WO/2019/062027
Kind Code:
A1
Abstract:
The present invention provides a green preparation method for N-substituted-L-pyroglutamic acid ester (I), comprising: using L-glutamic acid (II) as a starting material, and preparing L-glutamic acid diester hydrochloride (III) by means of an esterification reaction in the presence of an acidic reagent; and then subjecting L-glutamic acid diester hydrochloride (III) to N-substituted protective reaction with an N-substituent protective reagent by means of a one-pot method in the presence of a base and a solvent, introducing an N-substituted protective group, and heating is performed for dealcoholization cyclization in molecules to obtain N-substituted-L-pyroglutamic acid ester (I). The present invention has the advantages of cheap and easily available raw materials, classic reaction types, short process route, simple and convenient operation, small amount of waste water, green and environment-friendly production process, high reaction yield, and low product costs. 5R-benzyloxyaminopiperidine-2S-formate, 5R-benzyloxyaminopiperidine-2S-carboxylate oxalate, and avibactam can be prepared from N-substituted-L-pyroglutamic acid ester (I) prepared in the present invention.
Inventors:
QI YUXIN (CN)
QU HU (CN)
WANG BAOLIN (CN)
XU XIN (CN)
JU LIZHU (CN)
LI XINFA (CN)
QU HU (CN)
WANG BAOLIN (CN)
XU XIN (CN)
JU LIZHU (CN)
LI XINFA (CN)
Application Number:
PCT/CN2018/078071
Publication Date:
April 04, 2019
Filing Date:
March 06, 2018
Export Citation:
Assignee:
XINFA PHARMACEUTICAL CO LTD (CN)
International Classes:
C07D207/28
Foreign References:
CN107602436A | 2018-01-19 | |||
CN102127063A | 2011-07-20 | |||
CN102827058A | 2012-12-19 | |||
CN103998424A | 2014-08-20 |
Other References:
PAUL LE MAUX ET AL.: "Chemical reactivity of 6-diazo-5-oxo-L-norleucine (DON) catalyzed by metalloporphyrins (Fe, Ru", TETRAHEDRON, vol. 66, no. 25, 24 April 2010 (2010-04-24), pages 4462 - 4468, XP055362317, ISSN: 0040-4020, DOI: doi:10.1016/j.tet.2010.04.080
CAMILLE G. WERMUTH ET AL.: "2S, 4S)-2-Amino-4-(4, 4-diphenylbut-1-yl)-pentane-1, 5-dioic Acid: A Potent and Selective Antagonist for Metabotropic Glutamate Receptors Negatively Linked to Adenylate Cyclase", J. MED. CHEM., vol. 39, no. 4, 16 February 1996 (1996-02-16), pages 814 - 816, XP055588901
CAMILLE G. WERMUTH ET AL.: "2S, 4S)-2-Amino-4-(4, 4-diphenylbut-1-yl)-pentane-1, 5-dioic Acid: A Potent and Selective Antagonist for Metabotropic Glutamate Receptors Negatively Linked to Adenylate Cyclase", J. MED. CHEM., vol. 39, no. 4, 16 February 1996 (1996-02-16), pages 814 - 816, XP055588901
Attorney, Agent or Firm:
JINAN JINDI INTELLECTUAL PROPERTY AGENCY CO., LTD. et al. (CN)
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