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Method for preparing thioester compound

A technology of compounds and thioesters, which is applied in the field of preparation of thioesters, can solve the problems of expensive reducing agents or catalysts, harsh reaction conditions, unstable acylating reagents, etc., and achieve high selectivity, high reaction efficiency, and easy substrate The effect

Active Publication Date: 2021-03-02
JIANGXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These methods have the disadvantages of expensive reducing agents or catalysts, unstable acylating reagents, and harsh reaction conditions.

Method used

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  • Method for preparing thioester compound
  • Method for preparing thioester compound
  • Method for preparing thioester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (E)-S-1-(N,4-dimethylphenylsulfonamido)-2-(trimethylsilyl)vinylethanethioate(III-1)

[0031]

[0032] Add thioacetic acid I-1 (15mg, 0.2mmol), alkyne amide II-1 (62mg, 0.22mmol), DCM solvent 2mL in clean reaction tube, react at 0 ℃ for 6 hours (determine stop reaction with TLC time); after the reaction was finished, pure thioester III-1 was obtained through column chromatography separation, a light yellow liquid, and the yield was 90%.

[0033] 1 H NMR (400MHz, CDCl 3 )δ7.54(d, J=8.2Hz, 2H), 7.20(d, J=8.0Hz, 2H), 6.10(s, 1H), 2.73(s, 3H), 2.34(s, 3H), 2.08( s,3H),0.17(s,9H).

[0034] 13 C NMR (101MHz, CDCl 3 )δ193.5, 154.3, 144.7, 137.3, 135.7, 130.4, 129.1, 36.9, 31.0, 22.4, 0.0.

[0035] HRMS (ESI) calcd for C 15 h 23 NO 3 S 2 Si(M+Na) + :380.0781, found 380.0786.

Embodiment 2

[0037] (E)-S-1-(N,4-dimethylphenylsulfonamido)-2-(trimethyl silyl)vinyl 4-chlorobenzothioate(III-2)

[0038]

[0039] Add p-chlorothiophenylacetic acid I-2 (34mg, 0.2mmol), alkyne amide II-1 (62mg, 0.22mmol), DCM solvent 2mL to a clean reaction tube, and react at 10°C for 5 hours (determined by TLC the time to stop the reaction); after the reaction was finished, the pure thioester III-2 was separated by column chromatography as a pale yellow oil with a yield of 87%.

[0040] 1 H NMR (400MHz, CDCl3) δ7.54(d, J=8.2Hz, 2H), 7.50(d, J=8.6Hz, 2H), 7.21(d, J=8.6Hz, 2H), 7.13(d, J =8.2Hz,2H),6.21(s,1H),2.77(s,3H),2.26(s,3H),0.17(s,9H).

[0041] 13 C NMR (100MHz, CDCl 3 )δ189.0, 155.4, 144.7, 140.9, 136.5, 135.6, 135.4, 130.4, 129.8, 129.6, 129.1, 37.3, 22.4, 0.0.

[0042] HRMS (ESI) calcd for C 20 h 24 ClNO 3 S 2 Si(M+Na) + :476.0548, found 476.0543.

Embodiment 3

[0044] (E)-S-1-(N,4–dimethylphenylsulfonamido)-2-(trimethylsilyl)vinylbenzothioate(III-3)

[0045]

[0046] Add thiophenylacetic acid I-3 (28 mg, 0.2 mmol), alkyne amide II-1 (62 mg, 0.22 mmol), and 2 mL of DCM solvent into a clean reaction tube, and react at 20° C. for 4 hours (use TLC to determine to stop the reaction) time); after the reaction was completed, pure thioester III-3 was obtained by column chromatography separation to obtain a colorless oil with a yield of 87%.

[0047] 1 H NMR (400MHz, CDCl 3 )δ7.59(t, J=8.1Hz, 4H), 7.43(t, J=7.4Hz, 1H), 7.27(t, J=7.8Hz, 2H), 7.16(d, J=8.1Hz, 2H) ,6.26(s,1H),2.82(s,3H),2.29(s,3H),0.21(s,9H).

[0048] 13 C NMR (101MHz, CDCl 3 )δ190.0, 155.1, 144.6, 137.1, 136.9, 135.6, 134.5, 130.3, 129.4, 129.1, 128.2, 37.2, 22.3, 0.0.

[0049] HRMS (ESI) calcd for C 20 h 25 NO 3 S 2 Si(M+Na) + :420.1118, found 420.1113.

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Abstract

The invention provides a method for preparing a thioester compound. The method comprises the following main step of: reacting silicon-based substituted endo-alkyne amide with monothiocarboxylic acid in an organic solvent to obtain a target product of which the reaction formula is (1). The method has the advantages of mild conditions, simple and easily available raw materials, wide application prospect and the like.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a method for preparing thioester compounds. Background technique [0002] Thioester is a class of active ester derivatives. This structural molecule plays an important role in the synthesis of polypeptides. It also exists in many drug molecules and natural product molecules. It is one of the important skeletons of many natural products and biologically active compounds. In terms of peptide synthesis, the natural ligation method proposed by the Kent group in 1994 (Science 1994, 266, 776–779) is a coupling of a polypeptide fragment with a thioester at the C-terminal and a cysteine-linked polypeptide fragment at the N-terminal. With the addition of thiol, a new natural amide bond was formed through the acyl transfer from S to N. This method is currently the most efficient method for chemically synthesizing proteins. Among pharmaceuticals, the discovery of sulfonamides and penicill...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C08G77/392
CPCC07F7/081C08G77/392Y02P20/55
Inventor 赵军锋姚超超
Owner JIANGXI NORMAL UNIV