Title:
PROCESS FOR PRODUCTION OF MONO-SUBSTITUTED ALKYLATED COMPOUND USING ALDIMINE OR DERIVATIVE THEREOF
Document Type and Number:
WIPO Patent Application WO/2007/013698
Kind Code:
A1
Abstract:
Disclosed is a process for producing an asymmetric mono-substituted alkylated compound of an α-amino acid which is represented by a specific formula by using an aldimine-type Schiff base. In the process, the alkylation of an aldimine-type Schiff base in a medium in the presence of an optically active quaternary ammonium salt phase transfer catalyst and an inorganic base is started, and subsequently the reaction is quenched at any time preceding the completion of the stoichimetrical reaction, thereby yielding a mono-substituted alkylated product having a high optical purity.
Inventors:
MARUOKA KEIJI (JP)
INOUE TORU (JP)
MATSUMOTO JUN (JP)
INOUE TORU (JP)
MATSUMOTO JUN (JP)
Application Number:
PCT/JP2006/315457
Publication Date:
February 01, 2007
Filing Date:
July 28, 2006
Export Citation:
Assignee:
NAGASE & CO LTD (JP)
MARUOKA KEIJI (JP)
INOUE TORU (JP)
MATSUMOTO JUN (JP)
MARUOKA KEIJI (JP)
INOUE TORU (JP)
MATSUMOTO JUN (JP)
International Classes:
C07C249/02; B01J31/02; C07B53/00; C07B61/00; C07C227/04; C07C229/36; C07C251/24
Foreign References:
| JP2001048866A | 2001-02-20 | |||
| JP2002326992A | 2002-11-15 | |||
| JP2003081976A | 2003-03-19 | |||
| JP2004238362A | 2004-08-26 | |||
| JP2005041791A | 2005-02-17 |
Other References:
CHEN J.-T. ET AL.: "Synthesis of D-Phenylalanine Using Chiral Phase-Transfer Catalyst", YOUJI HUAXUE, vol. 8, no. 2, 1988, pages 164 - 166, XP003008262
MARUOKA K. ET AL.: "Enantioselective Amino Acid Synthesis by Chiral Phase-Transfer Catalysis", CHEMICAL REVIEW, vol. 103, no. 8, 2003, pages 3013 - 3028, XP003008263
OOI T. ET AL.: "Pratical Catalytic Enantioselective Syntheses of alpha,alpha-Dialkyl-alpha-amino Acids by Chiral Phase-Transfer Catalysis", J. AM. CHEM. SOC., vol. 122, no. 21, 2000, pages 5228 - 5229, XP002941729
BELOKON V.N. ET AL.: "Copper(II)salen catalysed, asymmetric synthesis of alpha,alpha-disubstituted amino acids", TETRAHEDRON, vol. 60, no. 8, 2004, pages 1849 - 1861, XP004488391
ARIMURA Y. ET AL.: "Design-gata Chiral Sokan Ido Shokubai o Mochiita Glycine Ester Aldimine Schiff Base no Ko-Enantio Sentakuteki Alkyl-ka Han'no no Kaihatsu", CSJ: THE CHEMICAL SOCIETY OF JAPAN DAI 86 SHUNKI NENKAI (2006) KOEN YOKOSHU II, 13 March 2006 (2006-03-13), pages 1073, XP003008264
See also references of EP 1930315A4
MARUOKA K. ET AL.: "Enantioselective Amino Acid Synthesis by Chiral Phase-Transfer Catalysis", CHEMICAL REVIEW, vol. 103, no. 8, 2003, pages 3013 - 3028, XP003008263
OOI T. ET AL.: "Pratical Catalytic Enantioselective Syntheses of alpha,alpha-Dialkyl-alpha-amino Acids by Chiral Phase-Transfer Catalysis", J. AM. CHEM. SOC., vol. 122, no. 21, 2000, pages 5228 - 5229, XP002941729
BELOKON V.N. ET AL.: "Copper(II)salen catalysed, asymmetric synthesis of alpha,alpha-disubstituted amino acids", TETRAHEDRON, vol. 60, no. 8, 2004, pages 1849 - 1861, XP004488391
ARIMURA Y. ET AL.: "Design-gata Chiral Sokan Ido Shokubai o Mochiita Glycine Ester Aldimine Schiff Base no Ko-Enantio Sentakuteki Alkyl-ka Han'no no Kaihatsu", CSJ: THE CHEMICAL SOCIETY OF JAPAN DAI 86 SHUNKI NENKAI (2006) KOEN YOKOSHU II, 13 March 2006 (2006-03-13), pages 1073, XP003008264
See also references of EP 1930315A4
Attorney, Agent or Firm:
NANJO, Hiromichi (Okina Bldg. 2-9, Nishitenma 3-chome, Kita-k, Osaka-shi Osaka 47, JP)
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