Title:
NOVEL C-SPIRO-O-GLYCOSIDE COMPOUND INTERMEDIATE AND PREPARATION METHOD THEREFOR
Document Type and Number:
WIPO Patent Application WO/2017/063327
Kind Code:
A1
Abstract:
The present invention provides a novel C-spiro-O-glycoside compound intermediate having a structural formula as shown in formula I. Also provided is a preparation method for the novel C-spiro-O-glycoside compound intermediate, comprising: first preparing 6-methyl-2-oxocyclohexyl-3-enecarboxylate; then preparing 3-bromo-6-methylsalicylic acid methyl ester; then preparing 2-methoxy-3-bromo-6-methylbenzoate; then preparing 2-methoxy-3-bromo-6-methylbenzoic acid; then preparing 3-bromo-methoxy-6-methyl-N, O-dimethyl hydroxybenzamide; then preparing (3-bromo-2-methoxy-6-methylphenyl)(4'-substituent benzyl)methanone; and then preparing (3-bromo-2-methoxy-6-methylphenyl)(4'-substituent benzyl)methane. The present invention avoids the formation of ortho/para isomers, and achieves a yield higher than 90%.
Inventors:
WU YUELIN (CN)
SUO QI (CN)
WANG ZIMEI (CN)
SUO QI (CN)
WANG ZIMEI (CN)
Application Number:
PCT/CN2016/075768
Publication Date:
April 20, 2017
Filing Date:
March 07, 2016
Export Citation:
Assignee:
SHANGHAI INST TECHNOLOGY (CN)
SHANGHAI XINPING MEDICALSCIENCE&TECHNOLOGY CO LTD (CN)
SHANGHAI XINPING MEDICALSCIENCE&TECHNOLOGY CO LTD (CN)
International Classes:
C07C43/225; C07C41/18; C07C45/45; C07C49/84
Domestic Patent References:
| WO2004063209A2 | 2004-07-29 |
Foreign References:
| CN105218329A | 2016-01-06 | |||
| CN104478670A | 2015-04-01 |
Other References:
LIU, YONGHAI ET AL.: "A New and Improved Process for C-aryl Glucoside SGLT2 Inhibitors", MONATSHEFTE FUR CHEMIE, vol. 10, no. 146, 11 April 2015 (2015-04-11), pages 1715 - 1721, XP035532552, ISSN: 1434-4475
P. V. BARVE ET AL.: "A Novel Synthesis of Bromomethoxy Disubstituted Derivatives of Benzocyclobutenone", INDIA JOURNAL OF CHEMISTY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, vol. 8, no. 43, 31 August 2004 (2004-08-31), ISSN: 0376-4699
HAUSER, F.M. ET AL.: "2-Hydroxy-6-Methylbenzoic Acid Derivatives", SYNTHESIS, vol. 10, 31 October 1980 (1980-10-31), pages 814 - 815, XP002149544, ISSN: 0039-7881
P. V. BARVE ET AL.: "A Novel Synthesis of Bromomethoxy Disubstituted Derivatives of Benzocyclobutenone", INDIA JOURNAL OF CHEMISTY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, vol. 8, no. 43, 31 August 2004 (2004-08-31), ISSN: 0376-4699
HAUSER, F.M. ET AL.: "2-Hydroxy-6-Methylbenzoic Acid Derivatives", SYNTHESIS, vol. 10, 31 October 1980 (1980-10-31), pages 814 - 815, XP002149544, ISSN: 0039-7881
Attorney, Agent or Firm:
CHANGZHOU BAIYETENGFEI PATENT AGENCY(GENERAL PARTNERSHIP) (CN)
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