Title:
METHOD FOR SYNTHESIZING N-SUBSTITUTED PHENYL-5-HYDROXYMETHYL-2-OXAZOLIDINONE
Document Type and Number:
WIPO Patent Application WO/2021/031533
Kind Code:
A1
Abstract:
Disclosed in the present invention is a method for synthesizing N-substituted phenyl-5-hydroxymethyl-2-oxazolidinone, wherein the synthesis method involves: 3-R 2-4-R 1-phenylamine and epoxy chloropropane being used as raw materials to carry out the reaction, and the N-substituted phenyl-5-hydroxymethyl-2-oxazolidinone being prepared, under alkaline conditions and a CO 2 atmosphere, from the resulting reaction product, wherein R 1 is a morpholine group, a morpholin-3-one group or piperazine and a derivative group thereof, and R 2 is a halogen, hydrogen or lower alkyl. The synthesis method provided by the present invention has the advantages of few steps, simple operation, inexpensive and easily available raw materials, mild reaction conditions, a high product yield, etc., and is particularly suitable for the industrial production of the intermediate of the antibiotic linezolid and the intermediate of the anti-thrombotic drug rivaroxaban.
Inventors:
YU DIHU (CN)
WANG QUAN (CN)
BAO LEI (CN)
HOU DAPENG (CN)
WANG QUAN (CN)
BAO LEI (CN)
HOU DAPENG (CN)
Application Number:
PCT/CN2020/074576
Publication Date:
February 25, 2021
Filing Date:
February 10, 2020
Export Citation:
Assignee:
HANGZHOU DIKE TECH CO LTD (CN)
International Classes:
C07D263/24
Domestic Patent References:
| WO1995007271A1 | 1995-03-16 | |||
| WO2012114355A1 | 2012-08-30 | |||
| WO2014045292A1 | 2014-03-27 |
Foreign References:
| CN105153059A | 2015-12-16 | |||
| CN103570640A | 2014-02-12 | |||
| CN103391927A | 2013-11-13 | |||
| CN1772750A | 2006-05-17 |
Other References:
YUSEOP LEE; JONGHOON CHOI; HYUNWOO KIM: "Stereocontrolled, Divergent, Al(III)-Catalyzed Coupling of Chiral N-Aryl Epoxy Amines and CO2", ORGANIC LETTERS, vol. 20, no. 16, 17 August 2018 (2018-08-17), pages 5039 - 5039, XP055570268, ISSN: 1523-7060, DOI: 10.1021/acs.orglett.8b02186
JEROEN RINTJEMA ,ROEL EPPING ,GIULIA FIORANI , EDDY MARTÍN ,EDUARDO C. ESCUDERO‐ADÁN ,ARJAN W. KLEIJ: "Substrate-Controlled Product Divergence: Conversion of CO2 into Heterocyclic Products", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 128, no. 12, 19 February 2016 (2016-02-19), pages 4040 - 4044, XP055781992, ISSN: 1521-3773, DOI: 10.1002/ange.201511521
YUMIKO OSA; YUKA HIKIMA; YOKO SATO; KOUICHI TAKINO; YOSHIHIRO IDA; SHUICHI HIRONO; HIROSHI NAGASE: "Convenient Synthesis of Oxazolidinones by the Use of Halomethyloxirane, Primary Amine, and Carbonate Salt", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 70, no. 14, 11 June 2005 (2005-06-11), pages 5737 - 5740, XP055498770, ISSN: 0022-3263, DOI: 10.1021/jo0501644
ORGANIC LETTERS, vol. 20, no. 16, 2018, pages 5036 - 5039
JOURNAL OF ORGANIC CHEMISTRY, vol. 70, no. 14, pages 5737 - 5740
ORGANIC LETTERS, vol. 201820, no. 16, pages 5036 - 5039
See also references of EP 4001268A4
JEROEN RINTJEMA ,ROEL EPPING ,GIULIA FIORANI , EDDY MARTÍN ,EDUARDO C. ESCUDERO‐ADÁN ,ARJAN W. KLEIJ: "Substrate-Controlled Product Divergence: Conversion of CO2 into Heterocyclic Products", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, vol. 128, no. 12, 19 February 2016 (2016-02-19), pages 4040 - 4044, XP055781992, ISSN: 1521-3773, DOI: 10.1002/ange.201511521
YUMIKO OSA; YUKA HIKIMA; YOKO SATO; KOUICHI TAKINO; YOSHIHIRO IDA; SHUICHI HIRONO; HIROSHI NAGASE: "Convenient Synthesis of Oxazolidinones by the Use of Halomethyloxirane, Primary Amine, and Carbonate Salt", THE JOURNAL OF ORGANIC CHEMISTRY, vol. 70, no. 14, 11 June 2005 (2005-06-11), pages 5737 - 5740, XP055498770, ISSN: 0022-3263, DOI: 10.1021/jo0501644
ORGANIC LETTERS, vol. 20, no. 16, 2018, pages 5036 - 5039
JOURNAL OF ORGANIC CHEMISTRY, vol. 70, no. 14, pages 5737 - 5740
ORGANIC LETTERS, vol. 201820, no. 16, pages 5036 - 5039
See also references of EP 4001268A4
Attorney, Agent or Firm:
HANGZHOU TIANQIN INTELLECTUAL PROPERTY AGENCY CO., LTD. (CN)
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