Ethanol → 2-[1-(5-Cyano-2-fluoro-phenyl)-2-(toluene-4-sulfonylamino)-vinyl]-cyclopropanecarboxylic acid ethyl ester

HRID 2416276Notes

Reaction equation

HRID 2416276 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9](=O)[C:10]1[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][C:11]=1[F:18])=[O:5])[CH3:2].[C:20]1([CH3:31])[CH:25]=[CH:24][C:23]([S:26]([NH:29]N)(=[O:28])=[O:27])=[CH:22][CH:21]=1.[CH2:32](O)C>>[CH2:1]([O:3][C:4]([CH:6]1[CH2:8][CH:7]1[C:9]([C:10]1[CH:15]=[C:14]([C:16]#[N:17])[CH:13]=[CH:12][C:11]=1[F:18])=[CH:32][NH:29][S:26]([C:23]1[CH:24]=[CH:25][C:20]([CH3:31])=[CH:21][CH:22]=1)(=[O:28])=[O:27])=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 15303P-ToluenesulfonylhydrazideHCID 698411172-(5-Cyano-2-fluoro-benzoyl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 698401482-[1-(5-Cyano-2-fluoro-phenyl)-2-(toluene-4-sulfonylamino)-vinyl]-cyclopropanecarboxylic acid ethyl esterYield 66%

Procedure

2-(5-cyano-2-fluoro-benzoyl)-cyclopropanecarboxylic acid ethyl ester (1.62 g, 6.2 mmol) and p-toluenesulfonhydrazide (2.31 g, 12.4 mmol) were refluxed in 50 mL ethanol for 36 h. The reaction was concentrated in vacuo, then purified by flash chromatography on silica gel using ethyl acetate/hexane (0-25%) as the eluent to give 2-[1-(5-cyano-2-fluoro-phenyl)-2-(toluene-4-sulfonylamino)-vinyl]-cyclopropanecarboxylic acid ethyl ester (1.77 g, 66%) as a mixture of cis and trans isomers. 1H NMR (500 MHz, CDCl3) 7.87 (1H, d, J=8.24 Hz), 7.78 (0.5H, m), 7.76 (1H, d, J=8.24 Hz), 7.65 (0.5H, m), 7.61 (0.5H, dd, J=2.14, 6.71 Hz), 7.44 (0.5H, dd, J=2.14, 5.80 Hz), 7.36 (2H, dd, J=3.96, 7.93 Hz), 7.31 (0.5H, t, J=8.54 Hz), 7.18 (0.5H, t, J=8.54 Hz), 4.22 (1H, m), 4.12 (2H, dq, J=7.32, 4.27 Hz), 2.46 (3H, 2s), 2.20 (0.5H, m), 1.99 (0.5H, m), 1.66 (0.5H, m), 1.43 (0.5H, m), 1.31 (2H, m), 1.27 (3H, dt, J=7.02, 3.67 Hz). MS m/e 430.13 (M+H)+.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-34a52871bcc94da7ae271a21e3a25190
Source dataset
uspto-grants-2004_11
Patent number
US06822100B2

Reaction notes

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