Title:
METHOD FOR PRODUCING BIPHENYL COMPOUND
Document Type and Number:
WIPO Patent Application WO/2017/098975
Kind Code:
A1
Abstract:
A method for producing methyl (2Z)-3-(1,1'-biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]- prop-2-enoate, comprising the steps of: reacting 4-phenylbenzaldehyde with glycine in the presence of sodium hydroxide or potassium hydroxide to produce a reaction mixture, and then mixing the reaction mixture with hydrochloric acid to produce 2-amino-3-(1,1'-biphenyl-4-yl)-3-hydroxypropionic acid hydrochloride; reacting 2-amino-3-(1,1'-biphenyl-4-yl)-3-hydroxypropionic acid hydrochloride with di-tert-butyl dicarbonate under basic conditions to produce 3-(1,1'-biphenyl-4-yl)-2-[(tert- butoxycarbonyl)amino]-3-hydroxypropionic acid; reacting 3-(1,1'-biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]-3- hydroxypropionic acid with dimethyl sulfate in the presence of a base to produce methyl 3-(1,1'-biphenyl-4-yl)-2- [(tert-butoxycarbonyl)amino]-3-hydroxypropanoate; and reacting methyl 3-(1,1'-biphenyl-4-yl)-2-[(tert- butoxycarbonyl)amino]-3-hydroxypropanoate with methanesulfonyl chloride in the presence of a base to produce a corresponding mesyl-form compound, and then reacting the mesyl-form compound with sodium methylate to produce methyl (2Z)-3-(1,1'-biphenyl-4-yl)-2-[(tert-butoxycarbonyl)amino]- prop-2-enoate. According to the method, it becomes possible to produce methyl (2Z)-3-(1,1'-biphenyl-4-yl)-2- [(tert-butoxycarbonyl)amino]prop-2-enoate which is useful as an intermediate for the production of a medicine or the like.
Inventors:
SASAYAMA DAISUKE (JP)
MURAOKA HIDEO (JP)
AKIYAMA MASAKI (JP)
MURAOKA HIDEO (JP)
AKIYAMA MASAKI (JP)
Application Number:
PCT/JP2016/085502
Publication Date:
June 15, 2017
Filing Date:
November 30, 2016
Export Citation:
Assignee:
SUMITOMO CHEMICAL CO (JP)
International Classes:
C07C269/06; C07C271/22; C07B53/00
Domestic Patent References:
| WO2016199688A1 | 2016-12-15 |
Foreign References:
| GB762240A | 1956-11-28 | |||
| JPS60190749A | 1985-09-28 | |||
| JP2003342251A | 2003-12-03 |
Other References:
DIETER ENDERS ET AL.: "Asymmetric Synthesis of alpha-Substituted N-Methylsulfonamides", HELVETICA CHIMICA ACTA, vol. 85, no. 11, 2002, pages 3657 - 3677, XP055392187
ZHI-TAO HE ET AL.: "Copper-Catalyzed Asymmetric Hydroboration of alpha-Dehydroamino Acid Derivatives: Facile Synthesis of Chiral beta- Hydroxy-alpha-amino Acids", ORGANIC LETTERS, vol. 16, 14 February 2014 (2014-02-14), pages 1426 - 1429, XP055392189
ZHI-TAO HE ET AL.: "Copper-Catalyzed Asymmetric Hydroboration of alpha-Dehydroamino Acid Derivatives: Facile Synthesis of Chiral beta- Hydroxy-alpha-amino Acids", ORGANIC LETTERS, vol. 16, 14 February 2014 (2014-02-14), pages 1426 - 1429, XP055392189
Attorney, Agent or Firm:
NAKAYAMA, Tohru et al. (JP)
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