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Title:
METHOD FOR PREPARING 5R-BENZYLOXYAMINOPIPERIDIN-2S-CARBOXYLIC ACID OR DERIVATIVE THEREOF
Document Type and Number:
WIPO Patent Application WO/2019/127902
Kind Code:
A1
Abstract:
The present invention relates to a green method for preparing 5R-benzyloxyaminopiperidin-2S-carboxylic acid or derivatives thereof. According to the method, L-glutamic acid, used as a starting raw material, is subjected to esterification in the presence of an acidic reagent, and is then successively reacted with 2-haloacetate and an N-protective reagent, or the N-protective reagent and the 2-haloacetate under alkaline conditions to obtain a compound IV, wherein same is then subjected to ring formation by intramolecular condensation under the action of strong base to obtain an N-protective group piperidin-5-one-2S-carboxylate (V). The resulting compound V is sujected to one of the following routes for preparing the 5R-benzyloxyaminopiperidin-2S-carboxylic acid (or carboxylate): route 1: the compound V is subjected to protective group-removing, condensation with a benzyloxy ammonia hydrochloride, imine-reduction-chiral resolution, neutralization, and hydrolysis; route 2: hydrolysis of the compound V, protective group removing, condensation of benzyloxy ammonia hydrochloride, reduction-chiral resolution of imine, and neutralization; and route 3: the compound V is subjected to condensation with benzyloxy ammonia hydrochloride, imine-reduction-chiral resolution, protective group-removing, neutralization, and hydrolysis. This route can be achieved by a "one pot method".

Inventors:
QI, Yuxin (Huangdian Village, Kenli Town Kenli Count, Dongying Shandong 0, 257500, CN)
LI, Xinfa (Huangdian Village, Kenli Town Kenli Count, Dongying Shandong 0, 257500, CN)
XU, Xin (Huangdian Village, Kenli Town Kenli Count, Dongying Shandong 0, 257500, CN)
WANG, Baolin (Huangdian Village, Kenli Town Kenli Count, Dongying Shandong 0, 257500, CN)
QU, Hu (Huangdian Village, Kenli Town Kenli Count, Dongying Shandong 0, 257500, CN)
XIE, Shungen (Huangdian Village, Kenli Town Kenli Count, Dongying Shandong 0, 257500, CN)
Application Number:
CN2018/078072
Publication Date:
July 04, 2019
Filing Date:
March 06, 2018
Export Citation:
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Assignee:
XINFA PHARMACEUTICAL CO., LTD (Huangdian Village, Kenli Town Kenli Count, Dongying Shandong 0, 257500, CN)
International Classes:
C07D211/02; C07B57/00; C07D211/60; C07D211/68
Domestic Patent References:
WO2010126820A22010-11-04
WO2012172368A12012-12-20
Foreign References:
CN107540601A2018-01-05
US20100197928A12010-08-05
US20130012712A12013-01-10
US20140275001A12014-09-18
Attorney, Agent or Firm:
JINAN JINDI INTELLECTUAL PROPERTY AGENCY CO., LTD. (No. 27 Shanda Nan Rd, Licheng DistrictJinan, Shandong 9, 250199, CN)
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