Title:
PRODUCTION METHOD FOR HYDROXY-CARBOXYLIC ACID AMIDE COMPOUND, AND NOVEL ARYLBORONIC ACID COMPOUND
Document Type and Number:
WIPO Patent Application WO/2013/122130
Kind Code:
A1
Abstract:
Provided is a production method for a hydroxy-carboxylic acid amide compound, wherein a hydroxy-carboxylic acid amide compound is obtained by performing an amide condensation reaction between an α- or β-hydroxy-carboxylic acid compound and an amine compound, using as a catalyst an alkylboronic acid represented by R3B(OH)2 (in the formula, R3 is a primary alkyl group) or the arylboronic acid compound in formula (1) (in formula (1): -(CH2)nNR1R2 is bound to either the ortho-position or the para-position; n is either 1 or 2; R1 is a tertiary alkyl group; R2 is either a secondary or tertiary alkyl group; and -NR1R2 may form a ring). [Formula (1)]
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Inventors:
ISHIHARA KAZUAKI (JP)
SAKAKURA AKIRA (JP)
SAKAKURA AKIRA (JP)
Application Number:
PCT/JP2013/053500
Publication Date:
August 22, 2013
Filing Date:
February 14, 2013
Export Citation:
Assignee:
UNIV NAGOYA NAT UNIV CORP (JP)
International Classes:
C07C231/02; B01J31/02; C07C235/06; C07C235/16; C07C235/34; C07C235/36; C07C235/60; C07D211/16; C07F5/02; C07B61/00
Domestic Patent References:
| WO2004113351A2 | 2004-12-29 | |||
| WO2010103976A1 | 2010-09-16 | |||
| WO2012109749A1 | 2012-08-23 | |||
| WO2004113351A2 | 2004-12-29 |
Foreign References:
| JP2004506711A | 2004-03-04 | |||
| US20040010162A1 | 2004-01-15 | |||
| JPS6150A | 1986-01-06 | |||
| JP2002265472A | 2002-09-18 | |||
| JP2010538021A | 2010-12-09 |
Other References:
ISHIHARA ET AL.: "3,4,5-Trifluorobenzeneboronic Acid as an Extremely Active Amidation Catalyst", J. ORG. CHEM., vol. 61, no. 13, 1996, pages 4196 - 4197, XP000829573
KING ET AL.: "Defining the Structural Parameters That Confer Anticonvulsant Activity by the Site-by-Site Modification of (R)-N'-Benzyl 2-Amino-3-methylbutanamide", JOURNAL OF MEDICINAL CHEMISTRY, vol. 54, no. 19, 23 August 2011 (2011-08-23), pages 6432 - 6442, XP055141054
MAKI ET AL.: "New boron(III)-catalyzed amide and ester condensation reactions", TETRAHEDRON, vol. 63, 2007, pages 8645 - 8657, XP002542724
TANG P, BORIC ACID CATALYZED AMIDE FORMATION FROM CARBOXYLIC ACIDS AND AMINES: N-BENZYL- 4-PHENYLBUTYRAMIDE, ORGANIC SYNTHESES, vol. 81, 2005, pages 262, XP002519978
MYLAVARAPU ET AL.: "Boric Acid Catalyzed Amidation in the Synthesis of Active Pharmaceutical Ingredients", ORGANIC PROCESS RESEACH & DEVELOPMENT, vol. 11, no. 6, 2007, pages 1065 - 1068, XP055141063
PECANHA ET AL.: "Synthesis and anti-HIV activity of new C2 symmetric derivatives designed as HIV-1 protease inhibitors", IL FARMACO, vol. 58, no. 2, 2003, pages 149 - 157, XP055141065
AGWADA C. V.: "Potential Central Nervous System Active Agents. 1. Synthesis of Aromatic N-Benzyl Amides", J. CHEM. ENG. DATA, vol. 27, no. 4, 1982, pages 479 - 481, XP055141073
MARCELLI T.: "Machanistic Insights into Direct Amide Bond Formation Catalyzed by Boronic Acids: Halogens as Lewis Bases", ANGEW. CHEM. INT. ED., vol. 49, no. 38, 2010, pages 6840 - 6843, XP055141075
J. ORG. CHEM., vol. 61, 1996, pages 4196 - 4197
See also references of EP 2816026A4
KING ET AL.: "Defining the Structural Parameters That Confer Anticonvulsant Activity by the Site-by-Site Modification of (R)-N'-Benzyl 2-Amino-3-methylbutanamide", JOURNAL OF MEDICINAL CHEMISTRY, vol. 54, no. 19, 23 August 2011 (2011-08-23), pages 6432 - 6442, XP055141054
MAKI ET AL.: "New boron(III)-catalyzed amide and ester condensation reactions", TETRAHEDRON, vol. 63, 2007, pages 8645 - 8657, XP002542724
TANG P, BORIC ACID CATALYZED AMIDE FORMATION FROM CARBOXYLIC ACIDS AND AMINES: N-BENZYL- 4-PHENYLBUTYRAMIDE, ORGANIC SYNTHESES, vol. 81, 2005, pages 262, XP002519978
MYLAVARAPU ET AL.: "Boric Acid Catalyzed Amidation in the Synthesis of Active Pharmaceutical Ingredients", ORGANIC PROCESS RESEACH & DEVELOPMENT, vol. 11, no. 6, 2007, pages 1065 - 1068, XP055141063
PECANHA ET AL.: "Synthesis and anti-HIV activity of new C2 symmetric derivatives designed as HIV-1 protease inhibitors", IL FARMACO, vol. 58, no. 2, 2003, pages 149 - 157, XP055141065
AGWADA C. V.: "Potential Central Nervous System Active Agents. 1. Synthesis of Aromatic N-Benzyl Amides", J. CHEM. ENG. DATA, vol. 27, no. 4, 1982, pages 479 - 481, XP055141073
MARCELLI T.: "Machanistic Insights into Direct Amide Bond Formation Catalyzed by Boronic Acids: Halogens as Lewis Bases", ANGEW. CHEM. INT. ED., vol. 49, no. 38, 2010, pages 6840 - 6843, XP055141075
J. ORG. CHEM., vol. 61, 1996, pages 4196 - 4197
See also references of EP 2816026A4
Attorney, Agent or Firm:
ITEC INTERNATIONAL PATENT FIRM (JP)
Patent business corporation Itec international patent firm (JP)
Patent business corporation Itec international patent firm (JP)
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