Title:
PROCESS FOR PRODUCING OPTICALLY ACTIVE &agr -SUBSTITUTED CYSTEINE OR SALT THEREOF, INTERMEDIATE THEREFOR, AND PROCESS FOR PRODUCING THE SAME
Document Type and Number:
WIPO Patent Application WO/2004/031163
Kind Code:
A1
Abstract:
A practical process for easily or industrially advantageously producing from an easily available inexpensive material an optically active &agr -substituted cysteine or salt thereof useful as an intermediate for medicines, etc. The process, which is for producing an optically active &agr -substituted cysteine or salt thereof, comprises converting a cysteine derivative into a thiazoline compound, subjecting the compound to a stereoselective substituent-introducing reaction with the aid of an optically active quaternary ammonium salt, especially an axially asymmetric quaternary ammonium salt, as a catalyst to thereby obtain an optically active thiazoline compound, and hydrolyzing it.
Inventors:
MARUOKA KEIJI (JP)
OOI TAKASHI (JP)
INOUE KENJI (JP)
OOI TAKASHI (JP)
INOUE KENJI (JP)
Application Number:
PCT/JP2003/012565
Publication Date:
April 15, 2004
Filing Date:
October 01, 2003
Export Citation:
Assignee:
KANEKA CORP (JP)
MARUOKA KEIJI (JP)
OOI TAKASHI (JP)
INOUE KENJI (JP)
MARUOKA KEIJI (JP)
OOI TAKASHI (JP)
INOUE KENJI (JP)
International Classes:
B01J31/02; B01J31/40; C07D277/12; (IPC1-7): C07D277/12; B01J31/02; B01J38/00; C07C321/04; C07C321/08
Domestic Patent References:
| WO2000012493A1 | 2000-03-09 |
Foreign References:
| EP0045281A1 | 1982-02-03 | |||
| EP1302467A2 | 2003-04-16 |
Other References:
MULQUEEN, G.C. ET AL.: "Synthesis of the Thiazoline-based Siderophore (S)-Desferrithiocin.", TETRAHEDRON, vol. 49, no. 24, 1993, pages 5359 - 5364, XP001119496
BERGERON, R.J. ET AL.: "Effects of C-4 Stereochemistry and C-4' Hydroxylation on the Iron Clearing Efficiency and Toxcity of Desferrithiocin Analogues.", J. MED. CHEM., vol. 42, 1999, pages 2432 - 2440, XP002182656
ADAM, W ET AL: "Direct alpha-lithiation of 4,5-dihydro-1,3-thiazole-4-carboxylic Acids and Electrophilic Substitution.", SYNTHESIS, vol. 12, 1976, pages 817 - 819, XP002974962
EHRLER, J ET AL: "Total Synthesis of Thiangazole.", SYNLETT, vol. 9, 1994, pages 702 - 704, XP001119497
OOI, TAKASHI ET AL.: "Molecular Design of a C2-Symmetric Chiral Phase-Transfer Catalyst for Practical Asymmetric Synthesis of alpha-Amino Acids.", J. AM. CHEM. SOC., vol. 121, 1999, pages 6519 - 6520, XP002941730
OKINO, TOMOTAKA ET TAKEMOTO, YOSHIJI: "Asymmetic Alkylation of tert-Butyl Glycinate Schiff Base with Chiral Quaternary Ammonium Salt under Micellar Conditions.", ORGANIC LETTERS, vol. 3, no. 10, 2001, pages 1515 - 1517, XP002974963
OOI, TAKASHI: "Evaluation of the Efficiency of the Chiral Quaternary Ammonium Salt Beta-Np-NAS-Br in the Organic-Aqueous Phase-Transfer Alkylation of a Protected Glycine Derivative.", ADV.SYNTH.CATAL., vol. 344, no. 3-4, 2002, pages 288 - 291, XP002974964
See also references of EP 1548013A4
BERGERON, R.J. ET AL.: "Effects of C-4 Stereochemistry and C-4' Hydroxylation on the Iron Clearing Efficiency and Toxcity of Desferrithiocin Analogues.", J. MED. CHEM., vol. 42, 1999, pages 2432 - 2440, XP002182656
ADAM, W ET AL: "Direct alpha-lithiation of 4,5-dihydro-1,3-thiazole-4-carboxylic Acids and Electrophilic Substitution.", SYNTHESIS, vol. 12, 1976, pages 817 - 819, XP002974962
EHRLER, J ET AL: "Total Synthesis of Thiangazole.", SYNLETT, vol. 9, 1994, pages 702 - 704, XP001119497
OOI, TAKASHI ET AL.: "Molecular Design of a C2-Symmetric Chiral Phase-Transfer Catalyst for Practical Asymmetric Synthesis of alpha-Amino Acids.", J. AM. CHEM. SOC., vol. 121, 1999, pages 6519 - 6520, XP002941730
OKINO, TOMOTAKA ET TAKEMOTO, YOSHIJI: "Asymmetic Alkylation of tert-Butyl Glycinate Schiff Base with Chiral Quaternary Ammonium Salt under Micellar Conditions.", ORGANIC LETTERS, vol. 3, no. 10, 2001, pages 1515 - 1517, XP002974963
OOI, TAKASHI: "Evaluation of the Efficiency of the Chiral Quaternary Ammonium Salt Beta-Np-NAS-Br in the Organic-Aqueous Phase-Transfer Alkylation of a Protected Glycine Derivative.", ADV.SYNTH.CATAL., vol. 344, no. 3-4, 2002, pages 288 - 291, XP002974964
See also references of EP 1548013A4
Attorney, Agent or Firm:
Yasutomi, Yasuo (4-20 Nishinakajima 5-chome, Yodogawa-k, Osaka-shi Osaka, JP)
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