HCID 59432341, compound → 5-Ethyl-2-isopropoxycarbonylamino-4-trifluoromethyl-benzoic acid methyl ester

HRID 507050Notes

Reaction equation

HRID 507050 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH:10]=[CH2:11])[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[NH:16][C:17]([O:19][CH:20]([CH3:22])[CH3:21])=[O:18].[H][H]>[Pd].CO>[CH3:1][O:2][C:3](=[O:23])[C:4]1[CH:9]=[C:8]([CH2:10][CH3:11])[C:7]([C:12]([F:15])([F:14])[F:13])=[CH:6][C:5]=1[NH:16][C:17]([O:19][CH:20]([CH3:22])[CH3:21])=[O:18]

Participants

5

Reactant 2

HCID 59432341HCID 59432341, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 594322985-Ethyl-2-isopropoxycarbonylamino-4-trifluoromethyl-benzoic acid methyl esterYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Add 10% palladium on carbon (4.06 g, 12.22 mmol) to a solution of 2-isopropoxycarbonylamino-4-trifluoromethyl-5-vinyl-benzoic acid methyl ester (40.48 g, 122.19 mmol) in methanol (350 mL) in a Parr bottle. Subject the mixture to a hydrogen atmosphere at a pressure of 30 psi at room temperature with shaking on a Parr shaker apparatus for 2 h. Filter the mixture through Celite and remove the solvent under reduced pressure to provide the title compound as a white solid (39.07 g, 96%): TLC Rf 0.62 (3:1 hexanes/ethyl acetate); 1H NMR (CDCl3, 300 MHz) δ 1.13-1.42 (m, 9H), 2.71-2.80 (m, 2H), 3.89 (s, 3H), 5.21-5.27 (m, 1H), 7.98 (s, 1H), 8.81 (s, 1H), 10.23 (bs, 1H).

Workup

  1. customat room temperature
  2. filtrationFilter the mixture through Celite
  3. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-f604010d49024498822b0739bd48fe36
Source dataset
uspto-grants-2010_08
Patent number
US07786108B2

Reaction notes

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