Title:
REACTION AGENT FOR AMIDE REACTIONS AND AMIDE COMPOUND PRODUCTION METHOD USING SAME
Document Type and Number:
WIPO Patent Application WO/2021/085636
Kind Code:
A1
Abstract:
[Problem] To provide a novel means capable of generating highly stereoselective and/or highly efficient amidation reactions in a variety of substrates having a carboxyl group and an amino group, and capable of producing amide compounds. [Solution] A reaction agent for amide reactions between carboxyl groups and amino groups and including a silane compound indicated by general formula (A) and/or general formula (B). (In general formulas (A) and (B), each substituent represents the definition described in the Claims.)
Inventors:
YAMAMOTO HISASHI (JP)
MURAMATSU WATARU (JP)
HATTORI TOMOHIRO (JP)
MURAMATSU WATARU (JP)
HATTORI TOMOHIRO (JP)
Application Number:
PCT/JP2020/040960
Publication Date:
May 06, 2021
Filing Date:
October 30, 2020
Export Citation:
Assignee:
CHUBU UNIV EDUCATIONAL FOUNDATION (JP)
International Classes:
C07F7/04; C07C231/02; C07C233/05; C07C233/18; C07D223/12; C07F7/10; C07K1/08
Domestic Patent References:
| WO2019208731A1 | 2019-10-31 | |||
| WO2018199147A1 | 2018-11-01 |
Other References:
TOZAWA T., YAMANE YOSHINOBU, MUKAIYAMA TERUAKI: "An Efficient Method for the Preparation of Carboxamides by Dehydration Condensation Using-hexafluoro-2-propoxy)silane", vol. 34, no. 12, 1 January 2005 (2005-01-01), pages 1586 - 1587, XP055930633
TOZAWA TAKASHI, YAMANE YOSHINOBU, MUKAIYAMA TERUAKI: "A Convenient Method for Preparations of 1-Acylimidazoles and Carboxamides by Using Novel Imidazolylsilane Derivatives", CHEMISTRY LETTERS, CHEMICAL SOCIETY OF JAPAN,NIPPON KAGAKUKAI, JP, vol. 34, no. 5, 1 May 2005 (2005-05-01), JP , pages 734 - 735, XP055930635, ISSN: 0366-7022, DOI: 10.1246/cl.2005.734
SCHMIDT MICHAEL A., REIFF EMILY A., QIAN XINHUA, HANG CHAO, TRUC VU CHI, NATALIE KENNETH J., WANG CHENCHI, ALBRECHT JACOB, LEE AND: "Development of a Two-Step, Enantioselective Synthesis of an Amino Alcohol Drug Candidate", ORGANIC PROCESS RESEARCH & DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, US, vol. 19, no. 9, 2 July 2015 (2015-07-02), US , pages 1317 - 1322, XP055930641, ISSN: 1083-6160, DOI: 10.1021/acs.oprd.5b00192
CHEMICAL SOCIETY OF JAPAN: "NEW LECTURES ON EXPERIMENTAL CHEMISTRY", 30 November 2004, MARUZEN, TOKYO, , JP , ISBN: 4-621-07315-X, article CHEMICAL SOCIETY OF JAPAN (ED.): "Experimental Example 2.75, Experimental Example 2.86", pages: 259 - 260, 268-269, XP009536647
MURAMATSU WATARU, HATTORI TOMOHIRO, YAMAMOTO HISASHI: "Substrate-Directed Lewis-Acid Catalysis for Peptide Synthesis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 141, no. 31, 16 July 2019 (2019-07-16), pages 12288 - 12295, XP055930667, ISSN: 0002-7863, DOI: 10.1021/jacs.9b03850
MURAMATSU WATARU, MANTHENA CHAITANYA, NAKASHIMA ERIKA, YAMAMOTO HISASHI: "Peptide Bond-Forming Reaction via Amino Acid Silyl Esters: New Catalytic Reactivity of an Aminosilane", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 10, no. 16, 31 July 2020 (2020-07-31), US , pages 9594 - 9603, XP055930671, ISSN: 2155-5435, DOI: 10.1021/acscatal.0c02512
MURAMATSU WATARU, HATTORI TOMOHIRO, YAMAMOTO HISASHI: "Game Change from Reagent- to Substrate-Controlled Peptide Synthesis", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOCIETY OF JAPAN,NIPPON KAGAKUKAI, JP, vol. 93, no. 6, 15 June 2020 (2020-06-15), JP , pages 759 - 767, XP055930673, ISSN: 0009-2673, DOI: 10.1246/bcsj.20200057
ANNU. REV. BIOPHYS. BIOMOL. STRUCT., vol. 34, 2005, pages 91 - 118
TETRAHEDRON, vol. 6, 2005, pages 10827 - 10852
CHEM. REV., vol. 107, 2007, pages 5759 - 5812
CHEM. REV., vol. 111, 2011, pages 6557 - 6602
ORG. PROCESS RES. DEV., vol. 20, no. 2, 2016, pages 140 - 177
CHEM. REV., vol. 116, 2016, pages 12029 - 12122
SCIENCE, vol. 256, 1992, pages 221 - 225
ANGEW. CHEM. INT. ED., vol. 45, 2006, pages 1248 - 1252
BLANDEZ ET AL., CATALYSIS SCIENCE & TECHNOLOGY, vol. 5, 2015, pages 2167 - 2173
BONAR-LAW ET AL., TETRAHEDRON LETTERS, vol. 31, no. 46, 1990, pages 6725 - 6728
CORRU ET AL., JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 114, 1976, pages 135 - 144
DAVIS ET AL., TETRAHEDRON LETTERS, vol. 36, no. 18, 1995, pages 3269 - 3272
DUNNE ET AL., JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 42, 2011, pages 16782 - 16785
HORNER ET AL., JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 282, 1985, pages 155 - 174
See also references of EP 4053132A4
TOZAWA TAKASHI, YAMANE YOSHINOBU, MUKAIYAMA TERUAKI: "A Convenient Method for Preparations of 1-Acylimidazoles and Carboxamides by Using Novel Imidazolylsilane Derivatives", CHEMISTRY LETTERS, CHEMICAL SOCIETY OF JAPAN,NIPPON KAGAKUKAI, JP, vol. 34, no. 5, 1 May 2005 (2005-05-01), JP , pages 734 - 735, XP055930635, ISSN: 0366-7022, DOI: 10.1246/cl.2005.734
SCHMIDT MICHAEL A., REIFF EMILY A., QIAN XINHUA, HANG CHAO, TRUC VU CHI, NATALIE KENNETH J., WANG CHENCHI, ALBRECHT JACOB, LEE AND: "Development of a Two-Step, Enantioselective Synthesis of an Amino Alcohol Drug Candidate", ORGANIC PROCESS RESEARCH & DEVELOPMENT, AMERICAN CHEMICAL SOCIETY, US, vol. 19, no. 9, 2 July 2015 (2015-07-02), US , pages 1317 - 1322, XP055930641, ISSN: 1083-6160, DOI: 10.1021/acs.oprd.5b00192
CHEMICAL SOCIETY OF JAPAN: "NEW LECTURES ON EXPERIMENTAL CHEMISTRY", 30 November 2004, MARUZEN, TOKYO, , JP , ISBN: 4-621-07315-X, article CHEMICAL SOCIETY OF JAPAN (ED.): "Experimental Example 2.75, Experimental Example 2.86", pages: 259 - 260, 268-269, XP009536647
MURAMATSU WATARU, HATTORI TOMOHIRO, YAMAMOTO HISASHI: "Substrate-Directed Lewis-Acid Catalysis for Peptide Synthesis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 141, no. 31, 16 July 2019 (2019-07-16), pages 12288 - 12295, XP055930667, ISSN: 0002-7863, DOI: 10.1021/jacs.9b03850
MURAMATSU WATARU, MANTHENA CHAITANYA, NAKASHIMA ERIKA, YAMAMOTO HISASHI: "Peptide Bond-Forming Reaction via Amino Acid Silyl Esters: New Catalytic Reactivity of an Aminosilane", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 10, no. 16, 31 July 2020 (2020-07-31), US , pages 9594 - 9603, XP055930671, ISSN: 2155-5435, DOI: 10.1021/acscatal.0c02512
MURAMATSU WATARU, HATTORI TOMOHIRO, YAMAMOTO HISASHI: "Game Change from Reagent- to Substrate-Controlled Peptide Synthesis", BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, CHEMICAL SOCIETY OF JAPAN,NIPPON KAGAKUKAI, JP, vol. 93, no. 6, 15 June 2020 (2020-06-15), JP , pages 759 - 767, XP055930673, ISSN: 0009-2673, DOI: 10.1246/bcsj.20200057
ANNU. REV. BIOPHYS. BIOMOL. STRUCT., vol. 34, 2005, pages 91 - 118
TETRAHEDRON, vol. 6, 2005, pages 10827 - 10852
CHEM. REV., vol. 107, 2007, pages 5759 - 5812
CHEM. REV., vol. 111, 2011, pages 6557 - 6602
ORG. PROCESS RES. DEV., vol. 20, no. 2, 2016, pages 140 - 177
CHEM. REV., vol. 116, 2016, pages 12029 - 12122
SCIENCE, vol. 256, 1992, pages 221 - 225
ANGEW. CHEM. INT. ED., vol. 45, 2006, pages 1248 - 1252
BLANDEZ ET AL., CATALYSIS SCIENCE & TECHNOLOGY, vol. 5, 2015, pages 2167 - 2173
BONAR-LAW ET AL., TETRAHEDRON LETTERS, vol. 31, no. 46, 1990, pages 6725 - 6728
CORRU ET AL., JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 114, 1976, pages 135 - 144
DAVIS ET AL., TETRAHEDRON LETTERS, vol. 36, no. 18, 1995, pages 3269 - 3272
DUNNE ET AL., JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 133, no. 42, 2011, pages 16782 - 16785
HORNER ET AL., JOURNAL OF ORGANOMETALLIC CHEMISTRY, vol. 282, 1985, pages 155 - 174
See also references of EP 4053132A4
Attorney, Agent or Firm:
AOKI, Atsushi et al. (JP)
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