4-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pent-2-enoic acid ethyl ester → 4-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pentanoic acid ethyl ester

HRID 583415Notes

Reaction equation

HRID 583415 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH:5]=[CH:6][CH:7]([N:19]([CH3:36])[C:20](=[O:35])[C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)[CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[CH3:2]>O1CCCC1.[Pd]>[CH2:1]([O:3][C:4](=[O:37])[CH2:5][CH2:6][CH:7]([N:19]([CH3:36])[C:20](=[O:35])[C:21]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[C:23]([C:31]([F:33])([F:34])[F:32])[CH:22]=1)[CH2:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=1)[CH3:2]

Participants

4

Reactant 1

HCID 571817134-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pent-2-enoic acid ethyl ester

Product 1

HCID 542164914-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pentanoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 20.0 g of 4-[N-methyl-N-(3,5-bistrifluoromethyl-benzoyl)-amino]-5-(naphth-2-yl)-pent-2-enoic acid ethyl ester in 200 ml of tetrahydrofuran is hydrogenated at 20° C. for 2 hours in the presence of 1.0 g of palladium/activated carbon (10%). The reaction mixture is then filtered and concentrated by evaporation. In this way the title compound is obtained in the form of a colourless oil. Rf value=0.50 (hexane/ethyl acetate:1:1). IR(CH2Cl2) cm-1 : 2978, 1729, 1639, 1405, 1339, 1278, 1183, 1141, 903, 849, 820.

Workup

  1. filtrationThe reaction mixture is then filtered
  2. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1e8fb62e60224c85b3ef901a2bf37904
Source dataset
uspto-grants-1999_07
Patent number
US05929067

Reaction notes

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