HCID 54191973, compound → HCID 54514075, compound

HRID 583427Notes

Reaction equation

HRID 583427 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[CH:5]=[CH:6][CH:7]([N:21]([C:23](=[O:38])[C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[C:26]([C:34]([F:37])([F:36])[F:35])[CH:25]=1)[CH3:22])[CH:8]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:2].[H][H]>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH2:6][CH:7]([N:21]([C:23](=[O:38])[C:24]1[CH:29]=[C:28]([C:30]([F:31])([F:32])[F:33])[CH:27]=[C:26]([C:34]([F:36])([F:37])[F:35])[CH:25]=1)[CH3:22])[CH:8]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:2]

Participants

5

Reactant 2

HCID 54191973HCID 54191973, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54514075HCID 54514075, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 15.0 g (27.3 mmol) of 4-[N-(3,5-bistrifluoromethyl-benzoyl)-N-methylamino]-5,5-diphenyl-pent-2-enoic acid ethyl ester in 400 ml of tetrahydrofuran is hydrogenated with 1.5 g of 10% palladium on activated carbon under 1 atm. of hydrogen. After 4 hours the suspension is filtered over Hyflo and washed with tetrahydrofuran, and the filtrate is concentrated by evaporation. The title compound is obtained in the form of a yellow oil. TLC: ethyl acetate/hexane (1:2) Rf =0.50; Rt (HPLC)=22.4 min; 1H-NMR (400 MHz, d6 -DMSO, 120° C.) d 7.96 (br, 1H), 7.48-7.18 (m, 12H), 5.44 (br, 1H), 4.31 (d, 1H), 4.05 (q, 2H), 2.56 (br s, 3H), 2.44-2.27 (m, 2H), 1.93 (m, 1H), 1.76 (m, 1H), 1.17 (t, 3H); FAB-MS (M+H)+ =552.

Workup

  1. filtrationAfter 4 hours the suspension is filtered over Hyflo
  2. washwashed with tetrahydrofuran
  3. concentrationthe filtrate is concentrated by evaporation

Sources & evidence

ORD record
ord-de40b4b6a7464971b7d7634bdb7db791
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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