Title:
OXIDATIVE CLEAVAGE METHOD OF TROLOX AMIDE
Document Type and Number:
WIPO Patent Application WO/2024/071372
Kind Code:
A1
Abstract:
The present disclosure provides an oxidative cleavage method of a Trolox amide. More particularly, the disclosure provides a method for producing a compound of formula I, the method including a step for contacting a compound of formula II with an oxidant in a solvent, and a step for contacting the solvent with a base to promote the reaction of the compound of formula II with the oxidant. In the formulae: R1, R2, R3, R4, R5, R6, R7, R8 and R9 each independently represent a hydrogen atom, a halogen, an optionally substituted C1-6alkyl, an optionally substituted C1-6 alkoxy, or -C(=O)NRARB; and RA and RB each independently represent a hydrogen atom, an optionally substituted C1-6 alkyl, or an optionally substituted C1-6 alkoxy.
Inventors:
USUTANI HIROTSUGU (JP)
YAMAMOTO KENJI (JP)
HIRABAYASHI JUN (JP)
YAMAMOTO KENJI (JP)
HIRABAYASHI JUN (JP)
Application Number:
PCT/JP2023/035593
Publication Date:
April 04, 2024
Filing Date:
September 29, 2023
Export Citation:
Assignee:
SUMITOMO PHARMA CO LTD (JP)
PTC THERAPEUTICS INC (US)
PTC THERAPEUTICS INC (US)
International Classes:
C07C231/12; C07C235/78; C07D311/66
Domestic Patent References:
| WO2021167095A1 | 2021-08-26 |
Foreign References:
| JP2018500317A | 2018-01-11 | |||
| JP2020111582A | 2020-07-27 |
Other References:
GOROU ARAI: "Polarographic Studies on Oxidation of Hydroquinone due to Atmospheric Oxygen", DENKI KAGAKU OYOBI KOGYO BUTSURI KAGAKU, vol. 41, no. 6, 1 January 1973 (1973-01-01), pages 416 - 421, XP093154184
TADAYUKI TSUKATANI: "Measurement of Yeast Vitality Using Water-Soluble Tetrazolium Salt", DOJIN NEWS, vol. 127, 1 January 2008 (2008-01-01), pages 1 - 14, XP093154190
ROLLA N. HARGER: "THE OXIDATION OF HYDROQUINONE IN THE PRESENCE OF ALIPHATIC AMINES. FORMATION OF BIS(ALKYLAMINO) QUINONES", J. AM. CHEM. SOC., vol. 46, no. 11, 5 November 1924 (1924-11-05), pages 2540 - 2551, XP093154197
YOSHIDA, JUNICHI: "Development and application of microreactors", 2008
PATEL, A. NETSCHER, T. GILLE, L. MEREITER, K. ROSENAU, T.: "Novel tocopheryl compounds XXV: synthesis and comparison of the para-quinones of all four homologous tocopherol model compounds and their 3,4-dehydro derivatives", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 63, no. 24, 11 June 2007 (2007-06-11), AMSTERDAM, NL , pages 5312 - 5318, XP022261448, ISSN: 0040-4020, DOI: 10.1016/j.tet.2007.03.114
LADISLAV KURC: "Activity of basic catalysts in oxidation of 2-ethyl-5,6,7,8-tetrahydro-9,10-anthrahydroquinone", JOURNAL OF MOLECULAR CATALYSIS A CHEMICAL, ELSEVIER, AMSTERDAM., NL, vol. 202, no. 1-2, 1 August 2003 (2003-08-01), NL , pages 327 - 332, XP093154201, ISSN: 1381-1169, DOI: 10.1016/S1381-1169(03)00250-4
L. KURC: "Catalytic oxidation of 2-ethyl-5,6,7,8-tetrahydro-9,10-anthrahydroquinone", RESEARCH ON CHEMICAL INTERMEDIATES, AMSTERDAM, NL, vol. 27, no. 3, 1 April 2001 (2001-04-01), NL , pages 249 - 258, XP093154203, ISSN: 0922-6168, DOI: 10.1163/156856701300356464
TADAYUKI TSUKATANI: "Measurement of Yeast Vitality Using Water-Soluble Tetrazolium Salt", DOJIN NEWS, vol. 127, 1 January 2008 (2008-01-01), pages 1 - 14, XP093154190
ROLLA N. HARGER: "THE OXIDATION OF HYDROQUINONE IN THE PRESENCE OF ALIPHATIC AMINES. FORMATION OF BIS(ALKYLAMINO) QUINONES", J. AM. CHEM. SOC., vol. 46, no. 11, 5 November 1924 (1924-11-05), pages 2540 - 2551, XP093154197
YOSHIDA, JUNICHI: "Development and application of microreactors", 2008
PATEL, A. NETSCHER, T. GILLE, L. MEREITER, K. ROSENAU, T.: "Novel tocopheryl compounds XXV: synthesis and comparison of the para-quinones of all four homologous tocopherol model compounds and their 3,4-dehydro derivatives", TETRAHEDRON, ELSEVIER SIENCE PUBLISHERS, AMSTERDAM, NL, vol. 63, no. 24, 11 June 2007 (2007-06-11), AMSTERDAM, NL , pages 5312 - 5318, XP022261448, ISSN: 0040-4020, DOI: 10.1016/j.tet.2007.03.114
LADISLAV KURC: "Activity of basic catalysts in oxidation of 2-ethyl-5,6,7,8-tetrahydro-9,10-anthrahydroquinone", JOURNAL OF MOLECULAR CATALYSIS A CHEMICAL, ELSEVIER, AMSTERDAM., NL, vol. 202, no. 1-2, 1 August 2003 (2003-08-01), NL , pages 327 - 332, XP093154201, ISSN: 1381-1169, DOI: 10.1016/S1381-1169(03)00250-4
L. KURC: "Catalytic oxidation of 2-ethyl-5,6,7,8-tetrahydro-9,10-anthrahydroquinone", RESEARCH ON CHEMICAL INTERMEDIATES, AMSTERDAM, NL, vol. 27, no. 3, 1 April 2001 (2001-04-01), NL , pages 249 - 258, XP093154203, ISSN: 0922-6168, DOI: 10.1163/156856701300356464
Attorney, Agent or Firm:
KAMADA, Mitsunori et al. (JP)
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