Toluene → HCID 178500456, compound

HRID 2118258Notes

Reaction equation

HRID 2118258 reaction equation
C([C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][N:10]([CH3:24])[S:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH2:5][CH2:4]1)=O.C1(P(=[CH:44][C:45]([O:47][CH3:48])=[O:46])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:49]1(C)C=CC=CC=1>>[CH3:48][O:47][C:45](=[O:46])[CH:44]=[CH:49][C@H:3]1[CH2:8][CH2:7][C@H:6]([CH2:9][N:10]([CH3:24])[S:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)(=[O:13])=[O:12])[CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 1140TolueneHCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 178484050HCID 178484050, compound

Product 1

HCID 178500456HCID 178500456, compoundYield 91%

Procedure

2 g (5.5 mmol) of trans-N-(4-formyl-cyclohexylmethyl)-N-methyl-4-trifluoromethyl-benzenesulfonamide and 2.2 g (6.6 mmol, 1.2 eq) of methyl (triphenyl-phosphoranylidene)acetate in 25 mL of toluene were stirred at 90° C. for 1 h. The solution was concentrated and chromatographed on silicagel with CH2Cl2:Et2O 95:5 as eluent, giving 2.09 g (91%) of trans-3-(4-{[methyl-(4-trifluoromethyl-benzenesulfonyl)-amino]-methyl}-cyclohexyl)-acrylic acid methyl ester as an off white solid which was a mixture of E and Z isomers (98:2), MS: 437 (M+NH4+).

Workup

  1. concentrationThe solution was concentrated
  2. customchromatographed on silicagel with CH2Cl2:Et2O 95:5 as eluent

Sources & evidence

ORD record
ord-0fa27de594ed4b41b6ad0a7f57af7f7d
Source dataset
uspto-grants-2008_10
Patent number
US07442791B2

Reaction notes

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