Title:
METHOD FOR PREPARING TRETINOIN
Document Type and Number:
WIPO Patent Application WO/2021/139615
Kind Code:
A1
Abstract:
Disclosed in the present invention is a method for preparing tretinoin. The method comprises the following steps: 1) hydrolysing vitamin A acetate in alkaline conditions to obtain vitamin A; and 2) in an oxygen atmosphere, implementing an oxidation reaction of the vitamin A in ionic liquid bis-(3-methyl-1-imidazole)ethylene tetrafluoroborate under the catalysing action of RuCl2(PPh3)3 to obtain tretinoin. The present invention has mild reaction conditions, the reaction raw materials are easy to obtain, the intermediate does not require purification, the reaction yield reaches as high as 90%, and the purity reaches 99%, having good prospects for industrial application.
Inventors:
SHI NING (CN)
LIU HONGLIANG (CN)
LIU WENTING (CN)
MA GUANGBIN (CN)
HUANG LIBIN (CN)
ZHANG XIANXIAN (CN)
LIU HONGLIANG (CN)
LIU WENTING (CN)
MA GUANGBIN (CN)
HUANG LIBIN (CN)
ZHANG XIANXIAN (CN)
Application Number:
PCT/CN2021/070073
Publication Date:
July 15, 2021
Filing Date:
January 04, 2021
Export Citation:
Assignee:
SHANDONG LIANGFU PHARMACEUTICAL CO LTD (CN)
International Classes:
C07C403/20
Foreign References:
| US3746730A | 1973-07-17 | |||
| CN1309120A | 2001-08-22 | |||
| CN109731612A | 2019-05-10 | |||
| JPH05271184A | 1993-10-19 | |||
| DE4440286A1 | 1996-05-15 |
Other References:
BEHR A, EUSTERWIEMANN K: "Ruthenium-catalyzed oxidation of primary alcohols with the new oxidation system N-methylmorpholine/hydrogen peroxide", JOURNAL OF ORGANOMETALLIC CHEMISTRY, ELSEVIER B.V, LAUSANNE, 1 January 1991 (1991-01-01), Lausanne, pages 215 - 219, XP055827437, DOI: 10.1016/0022-328X(91)83102-A
HIDEO TANAKA, HIROYUKI KAGECHIKA, EMIKO KAWACHI, HIROSHI FUKASAWA, YUICHI HASHIMOTO, KOICHI SHUDO: "Base-catalyzed isomerization of retinoic acid. Synthesis and differentiation-inducing activities of 14-alkylated all-trans-, 13-cis-, and 20,14-retro-retinoic acids", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 35, no. 3, 1 February 1992 (1992-02-01), pages 567 - 572, XP055366003, ISSN: 0022-2623, DOI: 10.1021/jm00081a020
YOSHIAKI NISHIBAYASHI ET AL.: "Extremely high enantioselective redox reaction of ketones and alcohols catalyzed by RuCl2(PPh3)(oxazolinylferrocenylphosphine)", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, vol. 18, 1 January 1999 (1999-01-01), pages 2291 - 93, XP002275450, ISSN: 0276-7333, DOI: 10.1021/om990210o
HIDEO TANAKA, HIROYUKI KAGECHIKA, EMIKO KAWACHI, HIROSHI FUKASAWA, YUICHI HASHIMOTO, KOICHI SHUDO: "Base-catalyzed isomerization of retinoic acid. Synthesis and differentiation-inducing activities of 14-alkylated all-trans-, 13-cis-, and 20,14-retro-retinoic acids", JOURNAL OF MEDICINAL CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 35, no. 3, 1 February 1992 (1992-02-01), pages 567 - 572, XP055366003, ISSN: 0022-2623, DOI: 10.1021/jm00081a020
YOSHIAKI NISHIBAYASHI ET AL.: "Extremely high enantioselective redox reaction of ketones and alcohols catalyzed by RuCl2(PPh3)(oxazolinylferrocenylphosphine)", ORGANOMETALLICS, AMERICAN CHEMICAL SOCIETY, vol. 18, 1 January 1999 (1999-01-01), pages 2291 - 93, XP002275450, ISSN: 0276-7333, DOI: 10.1021/om990210o
Attorney, Agent or Firm:
JEEKAI&PARTNERS (CN)
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