Title:
DEUTERIUM-ENRICHED COMPOSITION, DEUTERIUM-SUBSTITUTED CARBOXYLIC ACID PRODUCTION METHOD, REACTION ACCELERATOR, AND USE OF COMPOUND FOR CONVERTING CARBOXYLIC ACID TO ACID ANHYDRIDE
Document Type and Number:
WIPO Patent Application WO/2023/038093
Kind Code:
A1
Abstract:
Provided is a deuterium-enriched composition comprising a deuterium-substituted carboxylic acid or a salt thereof, wherein the carboxylic acid or the salt thereof includes an α hydrogen of a carboxy group and a hydrogen other than the α hydrogen bonded to a carbon, the deuterium substitution rate of the α hydrogen is not less than 5%, the deuterium substitution rate of the hydrogen other than the α hydrogen is not more than 3%, and when the carboxylic acid or the salt thereof comprises, in the molecule thereof, a group having a carbonyl group other than the carboxy group, the α hydrogen of the carbonyl group is not included in hydrogen other than the α hydrogen.
Inventors:
OHSHIMA TAKASHI (JP)
YAZAKI RYO (JP)
TANAKA TSUKUSHI (JP)
YAZAKI RYO (JP)
TANAKA TSUKUSHI (JP)
Application Number:
PCT/JP2022/033782
Publication Date:
March 16, 2023
Filing Date:
September 08, 2022
Export Citation:
Assignee:
UNIV KYUSHU NAT UNIV CORP (JP)
International Classes:
C07B59/00; C07C57/02; C07C57/38; C07C59/13; C07C59/205; C07C59/70; C07C59/84; C07C61/135; C07C61/29; C07C69/14; C07C69/44; C07C229/42; C07C233/47; C07C317/44; C07C323/62; C07D205/04; C07D207/337; C07D209/28; C07D209/48; C07D231/56; C07D263/32; C07D313/12; C07D491/052
Domestic Patent References:
| WO2020017569A1 | 2020-01-23 | |||
| WO2003053910A1 | 2003-07-03 |
Foreign References:
| JPH0921768A | 1997-01-21 | |||
| JP2020528892A | 2020-10-01 | |||
| US20090082417A1 | 2009-03-26 |
Other References:
DMITREVSKAYA, L.I. ET AL.: "New method for the α-deuteration of carboxylic acids", ZHURNAL ORGANICHESKOI KHIMII, MAIK NAUKA, MOSCOW, RU, vol. 19, no. 11, 1 January 1983 (1983-01-01), MOSCOW, RU , pages 1987 - 1989, XP009544435, ISSN: 0514-7492
LIU JIANBO, PARKER MATTHEW F.L., WANG SINAN, FLAVELL ROBERT R., TOSTE F. DEAN, WILSON DAVID M.: "Synthesis of N-trifluoromethyl amides from carboxylic acids", CHEM, CELL PRESS, US, vol. 7, no. 8, 1 August 2021 (2021-08-01), US , pages 2245 - 2255, XP093046648, ISSN: 2451-9294, DOI: 10.1016/j.chempr.2021.07.005
TANAKA TSUKUSHI, YAZAKI RYO, OHSHIMA TAKASHI: "Chemoselective Catalytic α-Oxidation of Carboxylic Acids: Iron/Alkali Metal Cooperative Redox Active Catalysis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 142, no. 9, 4 March 2020 (2020-03-04), pages 4517 - 4524, XP093046646, ISSN: 0002-7863, DOI: 10.1021/jacs.0c00727
SCHIRRA DOMINIC S., HIRSCHMANN MAX, RADULOV ILIYA A., LEHMANN MATTHIAS, THIELE CHRISTINA M.: "Investigations of the Alignment Process of PBPMLG: 2 H NMR Analysis Reveals a Thermoresponsive 90° Flip of the Polymer", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 60, no. 38, 13 September 2021 (2021-09-13), Hoboken, USA, pages 21040 - 21046, XP093046645, ISSN: 1433-7851, DOI: 10.1002/anie.202108814
MAJI ARUN, REDDI YERNAIDU, SUNOJ RAGHAVAN B., MAITI DEBABRATA: "Mechanistic Insights on Orthogonal Selectivity in Heterocycle Synthesis", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 8, no. 11, 2 November 2018 (2018-11-02), US , pages 10111 - 10118, XP093046644, ISSN: 2155-5435, DOI: 10.1021/acscatal.8b02537
TAYLER MICHAEL C. D., MARIE SABRINA, GANESAN A., LEVITT MALCOLM H.: "Determination of Molecular Torsion Angles Using Nuclear Singlet Relaxation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 132, no. 24, 23 June 2010 (2010-06-23), pages 8225 - 8227, XP093046642, ISSN: 0002-7863, DOI: 10.1021/ja1012917
HANSEN HANS-JÜRGEN, SLEWKA HANS-RICHARD, HUG WERNER: "On the Absolute Configuration of (+)-Indane-1-carboxylic Acid", HELVETICA CHIMICA ACTA, VERLAG HELVETICA CHIMICA ACTA., HOBOKEN, USA, vol. 65, no. 1, 3 February 1982 (1982-02-03), Hoboken, USA, pages 325 - 343, XP093046641, ISSN: 0018-019X, DOI: 10.1002/hlca.19820650135
CHANG TSUNG C., CADBERRY J. FREDERIC, LIGHTNER DAVID A.: "Stereospecific Bromine Replacement in the Synthesis of 4(e) and 4(a)-Deuterioadamantan-2-ones", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 14, no. 14, 1 December 1984 (1984-12-01), US , pages 1321 - 1332, XP009544434, ISSN: 0039-7911, DOI: 10.1080/00397918408057671
KADAM A. J., U. V. DESAI, R. B. MANE: "Synthesis of deuterium labelled acids", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY & SONS LTD., GB, vol. 42, no. 9, 20 September 1999 (1999-09-20), GB , pages 835 - 842, XP093046639, ISSN: 0362-4803, DOI: 10.1002/(SICI)1099-1344(199909)42:9<835::AID-JLCR244>3.0.CO;2-R
ADAM WALDEMAR, CUETO OMAR: "A Convenient and Efficient Preparation of Aromatic alpha-Hydroperoxy Acids via Oxygenation of alpha-Lithio Enolates, Prepared by Direct alpha-Lithiation of Arylacetic Acids", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 42, no. 1, 1 January 1977 (1977-01-01), pages 38 - 40, XP093046634, ISSN: 0022-3263, DOI: 10.1021/jo00421a007
ATKINSON JOSEPH G., JENO J. CSAKVARY, G. T. HERBERT, RONALD S. STUART: "Exchange reactions of carboxylic acid salts. Facile preparation of α-deuteriocarboxylic acids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 90, no. 2, 1 January 1968 (1968-01-01), pages 498 - 499, XP093046631, DOI: 10.1021/ja01004a054
YAKAZI, RYO: "Development and applied research of practical deuterium labeling reactions based on catalytic activation of ubiquitous carboxylic acids", 2020 ANNUAL REPORT, AMANO INSTITUTE OF TECHNOLOGY, JAPAN, 1 December 2021 (2021-12-01), Japan, pages 79 - 82, XP009544484
LIU JIANBO, PARKER MATTHEW F.L., WANG SINAN, FLAVELL ROBERT R., TOSTE F. DEAN, WILSON DAVID M.: "Synthesis of N-trifluoromethyl amides from carboxylic acids", CHEM, CELL PRESS, US, vol. 7, no. 8, 1 August 2021 (2021-08-01), US , pages 2245 - 2255, XP093046648, ISSN: 2451-9294, DOI: 10.1016/j.chempr.2021.07.005
TANAKA TSUKUSHI, YAZAKI RYO, OHSHIMA TAKASHI: "Chemoselective Catalytic α-Oxidation of Carboxylic Acids: Iron/Alkali Metal Cooperative Redox Active Catalysis", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 142, no. 9, 4 March 2020 (2020-03-04), pages 4517 - 4524, XP093046646, ISSN: 0002-7863, DOI: 10.1021/jacs.0c00727
SCHIRRA DOMINIC S., HIRSCHMANN MAX, RADULOV ILIYA A., LEHMANN MATTHIAS, THIELE CHRISTINA M.: "Investigations of the Alignment Process of PBPMLG: 2 H NMR Analysis Reveals a Thermoresponsive 90° Flip of the Polymer", ANGEWANDTE CHEMIE INTERNATIONAL EDITION, VERLAG CHEMIE, HOBOKEN, USA, vol. 60, no. 38, 13 September 2021 (2021-09-13), Hoboken, USA, pages 21040 - 21046, XP093046645, ISSN: 1433-7851, DOI: 10.1002/anie.202108814
MAJI ARUN, REDDI YERNAIDU, SUNOJ RAGHAVAN B., MAITI DEBABRATA: "Mechanistic Insights on Orthogonal Selectivity in Heterocycle Synthesis", ACS CATALYSIS, AMERICAN CHEMICAL SOCIETY, US, vol. 8, no. 11, 2 November 2018 (2018-11-02), US , pages 10111 - 10118, XP093046644, ISSN: 2155-5435, DOI: 10.1021/acscatal.8b02537
TAYLER MICHAEL C. D., MARIE SABRINA, GANESAN A., LEVITT MALCOLM H.: "Determination of Molecular Torsion Angles Using Nuclear Singlet Relaxation", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 132, no. 24, 23 June 2010 (2010-06-23), pages 8225 - 8227, XP093046642, ISSN: 0002-7863, DOI: 10.1021/ja1012917
HANSEN HANS-JÜRGEN, SLEWKA HANS-RICHARD, HUG WERNER: "On the Absolute Configuration of (+)-Indane-1-carboxylic Acid", HELVETICA CHIMICA ACTA, VERLAG HELVETICA CHIMICA ACTA., HOBOKEN, USA, vol. 65, no. 1, 3 February 1982 (1982-02-03), Hoboken, USA, pages 325 - 343, XP093046641, ISSN: 0018-019X, DOI: 10.1002/hlca.19820650135
CHANG TSUNG C., CADBERRY J. FREDERIC, LIGHTNER DAVID A.: "Stereospecific Bromine Replacement in the Synthesis of 4(e) and 4(a)-Deuterioadamantan-2-ones", SYNTHETIC COMMUNICATIONS, TAYLOR & FRANCIS INC., US, vol. 14, no. 14, 1 December 1984 (1984-12-01), US , pages 1321 - 1332, XP009544434, ISSN: 0039-7911, DOI: 10.1080/00397918408057671
KADAM A. J., U. V. DESAI, R. B. MANE: "Synthesis of deuterium labelled acids", JOURNAL OF LABELLED COMPOUNDS AND RADIOPHARMACEUTICALS, JOHN WILEY & SONS LTD., GB, vol. 42, no. 9, 20 September 1999 (1999-09-20), GB , pages 835 - 842, XP093046639, ISSN: 0362-4803, DOI: 10.1002/(SICI)1099-1344(199909)42:9<835::AID-JLCR244>3.0.CO;2-R
ADAM WALDEMAR, CUETO OMAR: "A Convenient and Efficient Preparation of Aromatic alpha-Hydroperoxy Acids via Oxygenation of alpha-Lithio Enolates, Prepared by Direct alpha-Lithiation of Arylacetic Acids", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 42, no. 1, 1 January 1977 (1977-01-01), pages 38 - 40, XP093046634, ISSN: 0022-3263, DOI: 10.1021/jo00421a007
ATKINSON JOSEPH G., JENO J. CSAKVARY, G. T. HERBERT, RONALD S. STUART: "Exchange reactions of carboxylic acid salts. Facile preparation of α-deuteriocarboxylic acids", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 90, no. 2, 1 January 1968 (1968-01-01), pages 498 - 499, XP093046631, DOI: 10.1021/ja01004a054
YAKAZI, RYO: "Development and applied research of practical deuterium labeling reactions based on catalytic activation of ubiquitous carboxylic acids", 2020 ANNUAL REPORT, AMANO INSTITUTE OF TECHNOLOGY, JAPAN, 1 December 2021 (2021-12-01), Japan, pages 79 - 82, XP009544484
Attorney, Agent or Firm:
HASEGAWA Yoshiki et al. (JP)
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