Title:
PROCESS FOR PREPARATION OF alpha-HYDROXYCARBOXYLIC ACID AMIDES
Document Type and Number:
WIPO Patent Application WO2003042166
Kind Code:
A3
Abstract:
The invention concerns a novel process for the preparation of 2-phenyl-2-hydroxy-N-[2-(3-alkoxy-4-hydroxyphenyl)-ethyl]-acetamides of the formula (I), wherein R1 is alkyl, R2 and R3 are each independently hydrogen or alkyl, and R4 is optionally substituted aryl or optionally substituted heteroaryl, which process comprises reacting a 2-(3-alkoxy-4-hydroxyphenyl)-ethylamine of the formula (II), wherein R1 R2 and R3 are as defined above with a alpha-hydoxycarboxylic acid ester of the formula (III) or a dioxolanone of the formula (III)a, wherein R4 is as defined above, and R5, R6 and R7 independently of each other are lower alkyl. The compounds of formula (I) are important intermediates for a novel group of fungicides derived from mandelic acid amides.
Inventors:
ZELLER MARTIN (CH)
FABER DOMINIK (CH)
VETTIGER THOMAS (CH)
LAMBERTH CLEMENS (CH)
FABER DOMINIK (CH)
VETTIGER THOMAS (CH)
LAMBERTH CLEMENS (CH)
Application Number:
PCT/EP2002/012844
Publication Date:
March 04, 2004
Filing Date:
November 15, 2002
Export Citation:
Assignee:
SYNGENTA PARTICIPATIONS AG (CH)
ZELLER MARTIN (CH)
FABER DOMINIK (CH)
VETTIGER THOMAS (CH)
LAMBERTH CLEMENS (CH)
ZELLER MARTIN (CH)
FABER DOMINIK (CH)
VETTIGER THOMAS (CH)
LAMBERTH CLEMENS (CH)
International Classes:
C07C231/02; C07C213/02; C07C231/00; C07C233/00; C07C235/08; C07C235/32; C07C235/34; C07D213/56; (IPC1-7): C07C231/02; C07C231/00; C07C235/34; C07C213/02
Domestic Patent References:
| WO2000041998A1 | 2000-07-20 | |||
| WO2001087822A1 | 2001-11-22 | |||
| WO1994029267A1 | 1994-12-22 |
Foreign References:
| GB2122617A | 1984-01-18 |
Other References:
REINER LUCKENBACH: "Beilsteins Handbuch der Organischen Chemie, 4th. Edition, Suppl. 4, vol. 13", 1985, SPRINGER-VERLAG, BERLIN HEIDELBERG NEW YORK TOKYO, XP002231833
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER CHEMISCHEN WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; XP002231834
E. MCDONALD ET AL.: "Synthesis of unsymmetrical dibenzylketones:....", TETRAHEDRON LETTERS., vol. 15, 1977, OXFORD GB, pages 1317 - 1320, XP002240441
SCHAFER H ET AL: "Enantioselective Conjugate Addition of Primary Dialkylzinc Reagents to 2-Aryl- and 2-Heteroaryl-nitroolefins Mediated by Titanium-TADDOLates Preparation of Enantioenriched 2-Aryl-alkylamines", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 51, no. 8, 20 February 1995 (1995-02-20), pages 2305 - 2324, XP004104805, ISSN: 0040-4020
PATENT ABSTRACTS OF JAPAN vol. 004, no. 081 (C - 014) 11 June 1980 (1980-06-11)
CHEMICAL ABSTRACTS, vol. 72, no. 11, 16 March 1970, Columbus, Ohio, US; abstract no. 54927n, SHETH ET AL.: "Synthesis of homovanillinamine by Clemmensen reduction." column 1; XP002240444
DATABASE WPI Section Ch Week 199441, Derwent World Patents Index; Class B04, AN 1994-330806, XP002240445
REINER LUCKENBACH: "Beilsteins Handbuch der Organischen Chemie, vol. XIII, 4th Edition, 4th Suppl., page 2603", 1985, SPRINGER-VERLAG, BERLIN HEIDELBERD NEW YORK TOKYO, XP002240443
PETER TINAPP: "Herstellung von Mandelaldehyden...", CHEMISCHE BERICHTE., vol. 104, no. 7, 1971, WEINHEIM DE, pages 2266 - 2272, XP002240442
JOHANNES S. BUCK: "Catalytic reduction of mandelonitriles", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 55, 1933, DC US, pages 2593 - 2597, XP001151934
DATABASE CROSSFIRE BEILSTEIN BEILSTEIN INSTITUT ZUR FOERDERUNG DER CHEMISCHEN WISSENSCHAFTEN, FRANKFURT AM MAIN, DE; XP002231834
E. MCDONALD ET AL.: "Synthesis of unsymmetrical dibenzylketones:....", TETRAHEDRON LETTERS., vol. 15, 1977, OXFORD GB, pages 1317 - 1320, XP002240441
SCHAFER H ET AL: "Enantioselective Conjugate Addition of Primary Dialkylzinc Reagents to 2-Aryl- and 2-Heteroaryl-nitroolefins Mediated by Titanium-TADDOLates Preparation of Enantioenriched 2-Aryl-alkylamines", TETRAHEDRON, ELSEVIER SCIENCE PUBLISHERS, AMSTERDAM, NL, vol. 51, no. 8, 20 February 1995 (1995-02-20), pages 2305 - 2324, XP004104805, ISSN: 0040-4020
PATENT ABSTRACTS OF JAPAN vol. 004, no. 081 (C - 014) 11 June 1980 (1980-06-11)
CHEMICAL ABSTRACTS, vol. 72, no. 11, 16 March 1970, Columbus, Ohio, US; abstract no. 54927n, SHETH ET AL.: "Synthesis of homovanillinamine by Clemmensen reduction." column 1; XP002240444
DATABASE WPI Section Ch Week 199441, Derwent World Patents Index; Class B04, AN 1994-330806, XP002240445
REINER LUCKENBACH: "Beilsteins Handbuch der Organischen Chemie, vol. XIII, 4th Edition, 4th Suppl., page 2603", 1985, SPRINGER-VERLAG, BERLIN HEIDELBERD NEW YORK TOKYO, XP002240443
PETER TINAPP: "Herstellung von Mandelaldehyden...", CHEMISCHE BERICHTE., vol. 104, no. 7, 1971, WEINHEIM DE, pages 2266 - 2272, XP002240442
JOHANNES S. BUCK: "Catalytic reduction of mandelonitriles", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY., vol. 55, 1933, DC US, pages 2593 - 2597, XP001151934
Download PDF: