4-[2-Benzyloxycarbonyl-2-(4-isobutyl-phenyl)-vinyl]-benzoic acid methyl ester → 4-[2-Carboxy-2-(4-isobutyl-phenyl)-ethyl]-benzoic acid methyl ester

HRID 2371279Notes

Reaction equation

HRID 2371279 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[C:11]([C:22]([O:24]CC2C=CC=CC=2)=[O:23])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1>C(O)(=O)C.[Pd]>[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH:11]([C:22]([OH:24])=[O:23])[C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=2)=[CH:8][CH:9]=1

Participants

4

Reactant 1

HCID 674864534-[2-Benzyloxycarbonyl-2-(4-isobutyl-phenyl)-vinyl]-benzoic acid methyl ester

Product 1

HCID 674865854-[2-Carboxy-2-(4-isobutyl-phenyl)-ethyl]-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 4-[2-Benzyloxycarbonyl-2-(4-isobutyl-phenyl)-vinyl]-benzoic acid methyl ester (1.8 g, 4.2 mmol) in acetic acid (30 mL) was added palladium on activated carbon (˜150 mg). The flask was purged with hydrogen and stirred under hydrogen atmosphere for 18 h. TLC and LC/MS analysis indicated that the reaction had gone to completion. The reaction was filtered through celite and concentrated by rotary evaporation. Toluene (100 mL) was added and the reaction was concentrated to dryness yielding 4-[2-Carboxy-2-(4-isobutyl-phenyl)-ethyl]-benzoic acid methyl ester as a colorless solid, 1.33 g (93%). LC-MS m/z=341 [C21H24O4+H]+.

Workup

  1. customThe flask was purged with hydrogen
  2. filtrationThe reaction was filtered through celite and
  3. concentrationconcentrated by rotary evaporation
  4. additionToluene (100 mL) was added
  5. concentrationthe reaction was concentrated to dryness

Sources & evidence

ORD record
ord-43b706ac629d4ce6b77f45249eb06623
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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