Title:
OXIDATION REACTION WITH EXCELLENT CONVERSION RATE
Document Type and Number:
WIPO Patent Application WO/2014/136730
Kind Code:
A1
Abstract:
A method of producing, at a high conversion rate and with good reproducibility, a 3‒[(S)‒7‒bromo‒2‒(2‒oxo‒propylamino)‒5‒pyridine‒2‒yl‒3H‒1,4‒benzodiazepine‒3‒yl]methyl propionate through the oxidization of a 3‒[(S)‒7‒bromo‒2‒(2‒hydroxy‒propylamino)‒5‒pyridine‒2‒yl‒3H‒benzo[e][1,4]diazepine‒3‒yl]methyl propionate by means of an oxidation catalyst is provided by regulating the ammonium ion content of the 3‒[(S)‒7‒bromo‒2‒(2‒hydroxy‒propylamino)‒5‒pyridine‒2‒yl‒3H‒benzo[e][1,4]diazepine‒3‒yl]methyl propionate.
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Inventors:
KAWAKAMI YUJI (JP)
MURASE TATSUSHI (JP)
TANAKA DAISUKE (JP)
YOSHIYAMA HIDEYUKI (JP)
KUWABE SHINITSU (JP)
MURASE TATSUSHI (JP)
TANAKA DAISUKE (JP)
YOSHIYAMA HIDEYUKI (JP)
KUWABE SHINITSU (JP)
Application Number:
PCT/JP2014/055329
Publication Date:
September 12, 2014
Filing Date:
March 03, 2014
Export Citation:
Assignee:
ONO PHARMACEUTICAL CO (JP)
International Classes:
C07D401/04; B01J31/02; C07D487/04; A61K31/5517; A61P25/02; A61P25/20; C07B61/00
Domestic Patent References:
| WO2011032692A1 | 2011-03-24 | |||
| WO2009145323A1 | 2009-12-03 | |||
| WO2010116794A1 | 2010-10-14 | |||
| WO2011032692A1 | 2011-03-24 | |||
| WO2000069836A1 | 2000-11-23 |
Foreign References:
| JP2011153104A | 2011-08-11 | |||
| JP2009542787A | 2009-12-03 | |||
| JP2002544266A | 2002-12-24 |
Other References:
SHIBUYA MASATOSHI ET AL.: "Oxidation of nitroxyl radicals: electrochemical and computational studies", TETRAHEDRON LETTERS, vol. 53, no. 16, 18 April 2012 (2012-04-18), pages 2070 - 2073, XP028468903, DOI: 10.1016/J.TETLET.2012.02.033
HAYASHI MASAKI ET AL.: "Oxidative Conversion of Silyl Enol Ethers to alpha, beta-Unsaturated Ketones Employing Oxoammonium Salts", ORGANIC LETTERS, vol. 14, no. 1, 1 January 2012 (2012-01-01), pages 154 - 157, XP055183107, DOI: 10.1021/OL2029417
MASAKI HAYASHI ET AL.: "9-Azanoradamantane N- Oxyl (Nor-AZADO): A Highly Active Organocatalyst for Alcohol Oxidation", CHEM. PHARM. BULL., vol. 59, no. 12, 1 January 2011 (2011-01-01), pages 1570 - 1573, XP055183110, DOI: 10.1248/CPB.59.1570
MASATOSHI SHIBUYA ET AL.: "Highly Efficient, Organocatalytic Aerobic Alcohol Oxidation", JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 133, no. 17, 1 January 2011 (2011-01-01), pages 6497 - 6500, XP055285577, DOI: 10.1021/JA110940C
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 128, 2006, pages 8412 - 8413
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, 2011, pages 6497 - 6500
CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 59, 2011, pages 1570 - 1573
SYNTHESIS, vol. 20, 2010, pages 3545 - 3555
JOURNAL OF ORGANIC CHEMISTRY, vol. 64, 1999, pages 2564 - 2566
RICHARD C. LAROCK: "Comprehensive Organic Transformations: A Guide to Functional Group Preparations 2nd Edition", 1999, JOHN WILEY & SONS INC
See also references of EP 2966069A4
HAYASHI MASAKI ET AL.: "Oxidative Conversion of Silyl Enol Ethers to alpha, beta-Unsaturated Ketones Employing Oxoammonium Salts", ORGANIC LETTERS, vol. 14, no. 1, 1 January 2012 (2012-01-01), pages 154 - 157, XP055183107, DOI: 10.1021/OL2029417
MASAKI HAYASHI ET AL.: "9-Azanoradamantane N- Oxyl (Nor-AZADO): A Highly Active Organocatalyst for Alcohol Oxidation", CHEM. PHARM. BULL., vol. 59, no. 12, 1 January 2011 (2011-01-01), pages 1570 - 1573, XP055183110, DOI: 10.1248/CPB.59.1570
MASATOSHI SHIBUYA ET AL.: "Highly Efficient, Organocatalytic Aerobic Alcohol Oxidation", JOURNAL OF AMERICAN CHEMICAL SOCIETY, vol. 133, no. 17, 1 January 2011 (2011-01-01), pages 6497 - 6500, XP055285577, DOI: 10.1021/JA110940C
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 128, 2006, pages 8412 - 8413
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, 2011, pages 6497 - 6500
CHEMICAL & PHARMACEUTICAL BULLETIN, vol. 59, 2011, pages 1570 - 1573
SYNTHESIS, vol. 20, 2010, pages 3545 - 3555
JOURNAL OF ORGANIC CHEMISTRY, vol. 64, 1999, pages 2564 - 2566
RICHARD C. LAROCK: "Comprehensive Organic Transformations: A Guide to Functional Group Preparations 2nd Edition", 1999, JOHN WILEY & SONS INC
See also references of EP 2966069A4
Attorney, Agent or Firm:
AOKI, Atsushi et al. (JP)
Aoki 篤 (JP)
Aoki 篤 (JP)
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