Title:
METHOD FOR PRODUCING N-ALKYL AMINO ACID AND PEPTIDE INCLUDING N-ALKYL AMINO ACID
Document Type and Number:
WIPO Patent Application WO/2023/127869
Kind Code:
A1
Abstract:
The present invention pertains to a method for producing a N-monoalkyl amino acid or an ester thereof, or a peptide including the N-monoalkyl amino acid or an ester thereof, the method comprising an alkylating step for mixing, in the presence of hydrogen and in a solvent: a starting amino acid or an ester thereof, or a peptide including the starting amino acid or an ester thereof; a C1-C6 primary alkylating agent or a substituted methyl halide; and a catalyst. The alkylating step is performed at a pressure of 1 atm or more, and is for generating a N-monoalkyl amino acid or an ester thereof, or a peptide including the N-monoalkyl amino acid or an ester thereof, obtained by binding a primary alkyl group corresponding to the C1-C6 primary alkylating agent or a substituted methyl halide with respect to the starting amino acid or an amino group of an ester thereof.
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Inventors:
KOMIYA SHIO (JP)
HOU ZENGYE (JP)
HOU ZENGYE (JP)
Application Number:
PCT/JP2022/048135
Publication Date:
July 06, 2023
Filing Date:
December 27, 2022
Export Citation:
Assignee:
CHUGAI PHARMACEUTICAL CO LTD (JP)
International Classes:
C07K1/02; C07B61/00; C07C227/18; A61K38/12; A61P35/00; C07C229/00; C07K7/64
Domestic Patent References:
| WO2000015656A1 | 2000-03-23 | |||
| WO2021090855A1 | 2021-05-14 |
Other References:
SAJIKI HIRONAO, IKAWA TAKASHI, HIROTA KOSAKU: "Reductive and Catalytic Monoalkylation of Primary Amines Using Nitriles as an Alkylating Reagent", ORGANIC LETTERS, AMERICAN CHEMICAL SOCIETY, US, vol. 6, no. 26, 1 December 2004 (2004-12-01), US , pages 4977 - 4980, XP093076189, ISSN: 1523-7060, DOI: 10.1021/ol047871o
TAKASHI IKAWA, YUKI FUJITA, TOMOTERU MIZUSAKI, SAE BETSUIN, HARUKI TAKAMATSU, TOMOHIRO MAEGAWA, YASUNARI MONGUCHI, HIRONAO SAJIKI: "Selective N-alkylation of amines using nitriles under hydrogenation conditions: facile synthesis of secondary and tertiary amines", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 10, no. 2, 1 January 2012 (2012-01-01), pages 293 - 304, XP055300329, ISSN: 1477-0520, DOI: 10.1039/C1OB06303K
HAN YINGLIN, CHOREV MICHAEL: "A Novel, One-Pot Reductive Alkylation of Amines by S -Ethyl Thioesters Mediated by Triethylsilane and Sodium Triacetoxyborohydride in the Presence of Palladium on Carbon", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 64, no. 6, 1 March 1999 (1999-03-01), pages 1972 - 1978, XP093076190, ISSN: 0022-3263, DOI: 10.1021/jo982125g
CHEN DIAO, DISOTUAR MARIA M., XIONG XIAOCHUN, WANG YUANXIANG, CHOU DANNY HUNG-CHIEH: "Selective N-terminal functionalization of native peptides and proteins", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 8, no. 4, 1 January 2017 (2017-01-01), United Kingdom , pages 2717 - 2722, XP055959934, ISSN: 2041-6520, DOI: 10.1039/C6SC04744K
TAKASHI IKAWA, YUKI FUJITA, TOMOTERU MIZUSAKI, SAE BETSUIN, HARUKI TAKAMATSU, TOMOHIRO MAEGAWA, YASUNARI MONGUCHI, HIRONAO SAJIKI: "Selective N-alkylation of amines using nitriles under hydrogenation conditions: facile synthesis of secondary and tertiary amines", ORGANIC & BIOMOLECULAR CHEMISTRY, ROYAL SOCIETY OF CHEMISTRY, vol. 10, no. 2, 1 January 2012 (2012-01-01), pages 293 - 304, XP055300329, ISSN: 1477-0520, DOI: 10.1039/C1OB06303K
HAN YINGLIN, CHOREV MICHAEL: "A Novel, One-Pot Reductive Alkylation of Amines by S -Ethyl Thioesters Mediated by Triethylsilane and Sodium Triacetoxyborohydride in the Presence of Palladium on Carbon", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 64, no. 6, 1 March 1999 (1999-03-01), pages 1972 - 1978, XP093076190, ISSN: 0022-3263, DOI: 10.1021/jo982125g
CHEN DIAO, DISOTUAR MARIA M., XIONG XIAOCHUN, WANG YUANXIANG, CHOU DANNY HUNG-CHIEH: "Selective N-terminal functionalization of native peptides and proteins", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 8, no. 4, 1 January 2017 (2017-01-01), United Kingdom , pages 2717 - 2722, XP055959934, ISSN: 2041-6520, DOI: 10.1039/C6SC04744K
Attorney, Agent or Firm:
HASEGAWA Yoshiki et al. (JP)
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