N-(2-Bromo-4-cyanophenyl)-2,2,2-trifluoroacetamide → (R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-(-N-(2-bromo-4-cyanophenyl)-N-trifluoroacetylamino)propene

HRID 975016Notes

Reaction equation

HRID 975016 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH:16]=[CH:17][CH2:18]O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:20][C:21]1[CH:33]=[C:32]([C:34]#[N:35])[CH:31]=[CH:30][C:22]=1[NH:23][C:24](=[O:29])[C:25]([F:28])([F:27])[F:26]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH:16]=[CH:17][CH2:18][N:23]([C:22]1[CH:30]=[CH:31][C:32]([C:34]#[N:35])=[CH:33][C:21]=1[Br:20])[C:24](=[O:29])[C:25]([F:26])([F:27])[F:28])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 19970261N-(2-Bromo-4-cyanophenyl)-2,2,2-trifluoroacetamideHCID 54485243(R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-hydroxypropene

Product 1

HCID 53953430(R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-(-N-(2-bromo-4-cyanophenyl)-N-trifluoroacetylamino)propene

Procedure

(R)-1-(N-Benzyloxycarbonylpyrrolidin-2-yl)-3-hydroxypropene and 2-bromo-4-cyano-N-trifluoroacetylaniline were used. Column chromatography using elution with a gradient of diethyl ether (5%-100%) in methylene chloride afforded the title compound as a clear, colorless oil: IR (CHCl3) 2231, 1702, 1157 cm-1 ; LRMS (m/z, relative intensity) 537 ([MH+ with 81Br], 13), 535 ([MH+ with 79Br], 13), 402 (29), 400 (30), 294 (55), 292 (57), 244 (80), 213 (89), 91 (100); Anal. calcd for C24BrF3H21N3O3.0.2 H2O: C, 53.39; H, 3.99; N, 7.78. Found: C, 53.25; H, 3.95; N, 7.98.

Workup

  1. washelution with a gradient of diethyl ether (5%-100%) in methylene chloride

Sources & evidence

ORD record
ord-feecc0ff712749a3912a20d773267ae5
Source dataset
uspto-grants-1997_03
Patent number
US05607951

Reaction notes

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