Title:
α-CARBONYL ALKENYL ESTER COMPOUND, PREPARATION METHOD THEREFOR AND APPLICATION THEREOF
Document Type and Number:
WIPO Patent Application WO/2021/169199
Kind Code:
A1
Abstract:
Provided are an α-carbonyl alkenyl ester compound and a preparation method therefor, and said compound is further used to react with a primary or secondary amine to prepare an amide compound. Said two reactions are combined to develop an amide bond and peptide bond formation method that use carboxylic acid and amine as starting materials and allenyl ketone as a condensing agent. The α-carbonyl alkenyl ester compound of an α-amino acid serves as a peptide synthesis building block and is used in peptide solid phase synthesis. The method has mild reaction conditions, is simple to operate, and has a high yield. Compared with existing amide bond condensation reagents, allenyl ketone has the advantages of being simple to prepare, having good stability, a low molecular weight, not racemizing when activating α-chiral carboxylic acid, and so on, and is a novel amide bond and peptide bond condensing agent.
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Inventors:
ZHAO JUNFENG (CN)
WANG ZHENGNING (CN)
WANG XUEWEI (CN)
WANG ZHENGNING (CN)
WANG XUEWEI (CN)
Application Number:
PCT/CN2020/110103
Publication Date:
September 02, 2021
Filing Date:
August 19, 2020
Export Citation:
Assignee:
UNIV JIANGXI NORMAL (CN)
International Classes:
C07C67/04; C07C69/00; C07C69/01; C07C69/608; C07C69/612; C07C69/76; C07C231/02; C07K1/04; C07K1/06
Foreign References:
| CN107141340A | 2017-09-08 |
Other References:
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HASHMI, A.S.K. BATS, J.W. CHOI, J.-H. SCHWARZ, L.: "Isomerizations on Silica Gel: Synthesis of Allenyl Ketones and the First Nazarov Cyclizations of Vinyl Allenyl Ketones", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 39, no. 41, 8 October 1998 (1998-10-08), Amsterdam , NL, pages 7491 - 7494, XP004134333, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(98)02057-7
LARKIN JOHN, MURRAY MICHAEL G, NONHEBEL DEREK C, MITCHELL ALASTAIR D: "Enol Benzoates of P-Diketones", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, ROYAL SOCIETY OF CHEMISTRY, CAMBRIDGE, UK, no. 4, 1 January 1976 (1976-01-01), Cambridge, UK, pages 380 - 383, XP055840824, ISSN: 0300-922X
MOON MALCOLM W., LARRY T. BELL, DAVID M. WEBSTER: "Acylation of Pyrroles and Tertiary Amides", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 39, no. 3, 31 December 1974 (1974-12-31), pages 315 - 318, XP055840826, ISSN: 0022-3263
WOODWARD R.B., R.A. OLOFSON, H. MAYER: "Stable Enol Esters from N-/-Butyl-5-methylisoxazolium Perchlorate", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 90, no. 5, 31 December 1968 (1968-12-31), pages 1371 - 1372, XP055840827, ISSN: 0002-7863
HASHMI, A.S.K. BATS, J.W. CHOI, J.-H. SCHWARZ, L.: "Isomerizations on Silica Gel: Synthesis of Allenyl Ketones and the First Nazarov Cyclizations of Vinyl Allenyl Ketones", TETRAHEDRON LETTERS, ELSEVIER, AMSTERDAM , NL, vol. 39, no. 41, 8 October 1998 (1998-10-08), Amsterdam , NL, pages 7491 - 7494, XP004134333, ISSN: 0040-4039, DOI: 10.1016/S0040-4039(98)02057-7
LARKIN JOHN, MURRAY MICHAEL G, NONHEBEL DEREK C, MITCHELL ALASTAIR D: "Enol Benzoates of P-Diketones", JOURNAL OF THE CHEMICAL SOCIETY, PERKIN TRANSACTIONS 1, ROYAL SOCIETY OF CHEMISTRY, CAMBRIDGE, UK, no. 4, 1 January 1976 (1976-01-01), Cambridge, UK, pages 380 - 383, XP055840824, ISSN: 0300-922X
MOON MALCOLM W., LARRY T. BELL, DAVID M. WEBSTER: "Acylation of Pyrroles and Tertiary Amides", THE JOURNAL OF ORGANIC CHEMISTRY, AMERICAN CHEMICAL SOCIETY, vol. 39, no. 3, 31 December 1974 (1974-12-31), pages 315 - 318, XP055840826, ISSN: 0022-3263
WOODWARD R.B., R.A. OLOFSON, H. MAYER: "Stable Enol Esters from N-/-Butyl-5-methylisoxazolium Perchlorate", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 90, no. 5, 31 December 1968 (1968-12-31), pages 1371 - 1372, XP055840827, ISSN: 0002-7863
Attorney, Agent or Firm:
BEIJING TROHENG INTELLECTUAL PROPERTY LAW FIRM (CN)
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