Title:
PRODUCTION METHOD FOR COMPOUND COMPRISING AMINO GROUP AND/OR HYDROXYL GROUP
Document Type and Number:
WIPO Patent Application WO/2013/129682
Kind Code:
A1
Abstract:
Provided is a production method in which a compound comprising an amino group and/or a hydroxyl group is generated under mild conditions by removing atom groups containing CO or CS from a substrate compound containing such atom groups. Atom groups containing CO or CS are removed by causing the compound represented by formula (I) to react, preferably in the presence of an ammonium salt, at a temperature of 120° C or less on a substrate compound (for example, an amide, a carbamate, or the like) comprising atom groups that contain CO or CS. With regards to formula (I), cases in which A is not present are possible, and in cases in which A is present, A represents an alkyl group having 1-6 carbon atoms. Formula (I): H2N-A-NH2.
Inventors:
OHSHIMA TAKASHI (JP)
MORIMOTO HIROYUKI (JP)
SHIMIZU YUHEI (JP)
MORIMOTO HIROYUKI (JP)
SHIMIZU YUHEI (JP)
Application Number:
PCT/JP2013/055845
Publication Date:
September 06, 2013
Filing Date:
March 04, 2013
Export Citation:
Assignee:
UNIV KYUSHU NAT UNIV CORP (JP)
International Classes:
C07C209/62; C07C29/128; C07C31/20; C07C41/18; C07C43/23; C07C211/27; C07C211/38; C07C211/52; C07C213/02; C07C215/30; C07C215/44; C07C215/52; C07C215/68; C07C215/76; C07C217/84; C07C227/06; C07C229/60; C07D209/16; C07D217/02; C07F7/18; C07B41/02; C07B43/04; C07B51/00
Foreign References:
| CN101463072A | 2009-06-24 | |||
| JP2007246400A | 2007-09-27 | |||
| US4507433A | 1985-03-26 |
Other References:
R.GEIGER ET AL.: "Abspaltung der N-Formylgruppe durch Hydrazin-acetat, Hydrazinderivate und Hydroxylamin", CHEMISCHE BERICHTE, vol. 101, no. 10, 1968, pages 3386 - 3391, XP055160370
G.EXCOFFIER. ET AL.: "Coupure sélective par l'hydrazine des groupements acétyles anoméres de résidus glycosyles acétyles", CARBOHYDRATE RESEARCH, vol. 39, no. 2, 1975, pages 368 - 373, XP055160377
E.CROS ET AL.: "N-Tetrachlorophthaloyl (TCP) Protection for Solid-Phase Peptide Synthesis", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 17, 2004, pages 3633 - 3642, XP055160379
Y.ISHIDO ET AL.: "Regioselective O-Deacetylation of Fully Acylated Glycosides and 1,2-O-Isopropylidenealdofuranose Derivatives with Hydrazine Hydrate", CARBOHYDRATE RESEARCH, vol. 97, no. 1, 1981, pages 51 - 79, XP055165289
D.H.R.BARTON ET AL.: "Nouvelle approche vers le squelette de l'acide lysergique à partir du beta-naphtol", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1988, pages 681 - 687, XP008174541
Y.SIMIZU ET AL.: "Microwave-Assisted Deacylation of Unactivated Amides Using Ammonium-Salt-Accelerated Transamidation", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 51, no. 34, 10 July 2012 (2012-07-10), pages 8564 - 8567, XP055160381
See also references of EP 2821389A4
ANGEW. CHEM., INT. ED., vol. 40, 2001, pages 598
ORG. LETT., vol. 14, 2012, pages 1386
G.EXCOFFIER. ET AL.: "Coupure sélective par l'hydrazine des groupements acétyles anoméres de résidus glycosyles acétyles", CARBOHYDRATE RESEARCH, vol. 39, no. 2, 1975, pages 368 - 373, XP055160377
E.CROS ET AL.: "N-Tetrachlorophthaloyl (TCP) Protection for Solid-Phase Peptide Synthesis", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 17, 2004, pages 3633 - 3642, XP055160379
Y.ISHIDO ET AL.: "Regioselective O-Deacetylation of Fully Acylated Glycosides and 1,2-O-Isopropylidenealdofuranose Derivatives with Hydrazine Hydrate", CARBOHYDRATE RESEARCH, vol. 97, no. 1, 1981, pages 51 - 79, XP055165289
D.H.R.BARTON ET AL.: "Nouvelle approche vers le squelette de l'acide lysergique à partir du beta-naphtol", BULLETIN DE LA SOCIETE CHIMIQUE DE FRANCE, 1988, pages 681 - 687, XP008174541
Y.SIMIZU ET AL.: "Microwave-Assisted Deacylation of Unactivated Amides Using Ammonium-Salt-Accelerated Transamidation", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION, vol. 51, no. 34, 10 July 2012 (2012-07-10), pages 8564 - 8567, XP055160381
See also references of EP 2821389A4
ANGEW. CHEM., INT. ED., vol. 40, 2001, pages 598
ORG. LETT., vol. 14, 2012, pages 1386
Attorney, Agent or Firm:
HIRAI Yasuo et al. (JP)
Yasuo Hirai (JP)
Yasuo Hirai (JP)
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Claims: