Title:
METHOD FOR PRODUCING 5-HYDROXYPIPERIDINE-2-CARBOXYLIC ACID
Document Type and Number:
WIPO Patent Application WO/2015/099126
Kind Code:
A1
Abstract:
A method for producing (2S,5S)/(2R,5R)-5-hydroxypiperidine-2-carboxylic acid indicated by formula (10), the method being characterized in including a step for removing protection from hydroxyl groups in a compound represented by formula (7) and synthesizing a compound represented by formula (8). (In the formula, P indicates a protecting group; R3 indicates an alkyl group having 1-4 carbon atoms; and A indicates an alkyl group having 1-10 carbon atoms, an aryl group having 6-12 carbon atoms, an alkyloxy group having 1-4 carbon atoms, or an aralkyloxy group having 7-20 carbon atoms.)
(In the formula, R3 indicates an alkyl group having 1-4 carbon atoms; and A indicates an alkyl group having 1-10 carbon atoms, an aryl group having 6-12 carbon atoms, an alkyloxy group having 1-4 carbon atoms, or an aralkyloxy group having 7-20 carbon atoms.)
Inventors:
TAKEHARA JUN (JP)
MURAI MASATO (JP)
OHTANI TAKASHI (JP)
MAEDA TOMOKO (JP)
HIDAKA TSUGIHIKO (JP)
MURAI MASATO (JP)
OHTANI TAKASHI (JP)
MAEDA TOMOKO (JP)
HIDAKA TSUGIHIKO (JP)
Application Number:
PCT/JP2014/084518
Publication Date:
July 02, 2015
Filing Date:
December 26, 2014
Export Citation:
Assignee:
API CORP (JP)
International Classes:
C07D211/60; C07C233/47; C07C309/66; C07D498/08; C07B61/00
Domestic Patent References:
| WO2009011551A2 | 2009-01-22 | |||
| WO2005014508A1 | 2005-02-17 | |||
| WO2010126820A2 | 2010-11-04 | |||
| WO2006125974A1 | 2006-11-30 | |||
| WO2014098188A1 | 2014-06-26 | |||
| WO2010126820A2 | 2010-11-04 | |||
| WO2006125974A1 | 2006-11-30 |
Foreign References:
| US6399600B1 | 2002-06-04 |
Other References:
JUNG, J. C. ET AL.: "DIASTEREOSELECTIVE SYNTHESIS OF (2S,5S)- AND (2S,5R)-N-BENZYLOXYCARBONYL-5-HYDROXYPIPECOLIC ACIDS FROM TRANS-4-HYDROXY-L-PROLINE", TETRAHEDRON : ASYMMETRY, vol. 17, no. 17, 2 October 2006 (2006-10-02), pages 2479 - 2486, XP024962414, DOI: 10.1016/J.TETASY.2006.07.035
HOARAU, S. ET AL.: "SYNTHESIS OF ENANTIOMERICALLY PURE (2R, 5S)- AND (2R, 5R)- 5-HYDROXYPIPECOLIC ACID FROM GLYCINATE SCHIFF BASES", TETRAHEDRON ASYMMETRY, vol. 7, no. 9, 1 September 1996 (1996-09-01), pages 2585 - 2593, XP004048331, DOI: 10.1016/0957-4166(96)00332-1
HERDEIS C. ET AL.: "AN EFFICIENT SYNTHETIC METHOD FOR THE PREPARATION OF (PLUS OR MINUS)-BAIKIAIN AND ITS DERIVATIVES", ARCHIV DER PHARMAZIE, vol. 326, no. 5, 1 January 1993 (1993-01-01), pages 297 - 301, XP008004122
JIANG B. ET AL.: "STEREOSELECTIVE SYNTHESIS OF KURZILACTONE AND DETERMINATION OF ITS ABSOLUTE CONFIGURATION", TETRAHEDRON : ASYMMETRY, vol. 12, no. 20, 13 November 2001 (2001-11-13), pages 2835 - 2843, XP004326382, DOI: 10.1016/S0957-4166(01)00506-7
KOBAYASHI Y. ET AL.: "SYNTHESIS OF MACROSPHELIDES H AND G", TETRAHEDRON LETTERS, vol. 43, no. 24, 10 June 2002 (2002-06-10), pages 4381 - 4384, XP004357600, DOI: 10.1016/S0040-4039(02)00781-5
LETAVIC M.A. ET AL.: "SYNTHESIS AND BIOLOGICAL ACTOVITY OF SELECTIVE PIPECOLIC ACID-BASED TNF-ALPHA CONVERTING ENZYME (TACE) INHIBITORS", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 10, 20 May 2002 (2002-05-20), pages 1387 - 1390, XP002762916
GRAHAM L. ET AL.: "SIMULTANEOUS DETERMINATION OF THE REDUCIBLE AND NONREDUCIBLE CROSS-LINKS OF CONNECTIVE TISSUE. ANALYSIS OF MINERALIZED AND NONMINERALIZED BONE COLLAGEN", BIOCHEMISTRY, vol. 28, no. 19, 1 January 1989 (1989-01-01), pages 7889 - 7895, XP055354097, DOI: 10.1021/BI00445A051
MARIN J. ET AL.: "DIASTEREOSELECTIVE HYDROXYLATION OF 6-SUBSTITUTED PIPERIDIN-2-ONES. AN EFFICIENTSYNTHESIS OF (2 S ,5 R )-5-HYDROXYLYSINE AND RELATED ?-AMINO ACIDS", JOURANL OF ORGANIC CHEMISTRY, vol. 67, no. 24, 1 January 2002 (2002-01-01), pages 8440 - 8449, XP055354102, DOI: 10.1021/JO025950C
P. D. BAILEY ET AL., CHEM. COMMUN., 1996, pages 349
P. D. BAILEY ET AL., TETRAHEDRON LETT., vol. 29, 1988, pages 2231
M. A. LETAVIC ET AL., BIOORG. MED. CHEM. LETT., vol. 12, 2002, pages 1387
TETRAHEDRON: ASYMMETRY, vol. 12, no. 12, 2001, pages 1713
See also references of EP 3091002A4
HOARAU, S. ET AL.: "SYNTHESIS OF ENANTIOMERICALLY PURE (2R, 5S)- AND (2R, 5R)- 5-HYDROXYPIPECOLIC ACID FROM GLYCINATE SCHIFF BASES", TETRAHEDRON ASYMMETRY, vol. 7, no. 9, 1 September 1996 (1996-09-01), pages 2585 - 2593, XP004048331, DOI: 10.1016/0957-4166(96)00332-1
HERDEIS C. ET AL.: "AN EFFICIENT SYNTHETIC METHOD FOR THE PREPARATION OF (PLUS OR MINUS)-BAIKIAIN AND ITS DERIVATIVES", ARCHIV DER PHARMAZIE, vol. 326, no. 5, 1 January 1993 (1993-01-01), pages 297 - 301, XP008004122
JIANG B. ET AL.: "STEREOSELECTIVE SYNTHESIS OF KURZILACTONE AND DETERMINATION OF ITS ABSOLUTE CONFIGURATION", TETRAHEDRON : ASYMMETRY, vol. 12, no. 20, 13 November 2001 (2001-11-13), pages 2835 - 2843, XP004326382, DOI: 10.1016/S0957-4166(01)00506-7
KOBAYASHI Y. ET AL.: "SYNTHESIS OF MACROSPHELIDES H AND G", TETRAHEDRON LETTERS, vol. 43, no. 24, 10 June 2002 (2002-06-10), pages 4381 - 4384, XP004357600, DOI: 10.1016/S0040-4039(02)00781-5
LETAVIC M.A. ET AL.: "SYNTHESIS AND BIOLOGICAL ACTOVITY OF SELECTIVE PIPECOLIC ACID-BASED TNF-ALPHA CONVERTING ENZYME (TACE) INHIBITORS", BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, vol. 12, no. 10, 20 May 2002 (2002-05-20), pages 1387 - 1390, XP002762916
GRAHAM L. ET AL.: "SIMULTANEOUS DETERMINATION OF THE REDUCIBLE AND NONREDUCIBLE CROSS-LINKS OF CONNECTIVE TISSUE. ANALYSIS OF MINERALIZED AND NONMINERALIZED BONE COLLAGEN", BIOCHEMISTRY, vol. 28, no. 19, 1 January 1989 (1989-01-01), pages 7889 - 7895, XP055354097, DOI: 10.1021/BI00445A051
MARIN J. ET AL.: "DIASTEREOSELECTIVE HYDROXYLATION OF 6-SUBSTITUTED PIPERIDIN-2-ONES. AN EFFICIENTSYNTHESIS OF (2 S ,5 R )-5-HYDROXYLYSINE AND RELATED ?-AMINO ACIDS", JOURANL OF ORGANIC CHEMISTRY, vol. 67, no. 24, 1 January 2002 (2002-01-01), pages 8440 - 8449, XP055354102, DOI: 10.1021/JO025950C
P. D. BAILEY ET AL., CHEM. COMMUN., 1996, pages 349
P. D. BAILEY ET AL., TETRAHEDRON LETT., vol. 29, 1988, pages 2231
M. A. LETAVIC ET AL., BIOORG. MED. CHEM. LETT., vol. 12, 2002, pages 1387
TETRAHEDRON: ASYMMETRY, vol. 12, no. 12, 2001, pages 1713
See also references of EP 3091002A4
Attorney, Agent or Firm:
KAWAGUCHI, Yoshiyuki et al. (JP)
Yoshiyuki Kawaguchi (JP)
Yoshiyuki Kawaguchi (JP)
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