3-[4-((S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propoxy)-phenyl]-propionic acid methyl ester → 3-(4-{(S)-2-[2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-3-phenyl-propoxy}-phenyl)-propionic acid methyl ester

HRID 1452701Notes

Reaction equation

HRID 1452701 reaction equation
[CH3:1][O:2][C:3](=[O:49])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C@@H:14]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:38]CC3C=CC(OC)=CC=3)([C:34]([F:37])([F:36])[F:35])[C:30]([F:33])([F:32])[F:31])=[CH:25][C:24]=2[CH3:48])[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:8][CH:7]=1>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:49])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][C@@H:14]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([OH:38])([C:30]([F:33])([F:32])[F:31])[C:34]([F:35])([F:36])[F:37])=[CH:25][C:24]=2[CH3:48])[CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 866042313-[4-((S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propoxy)-phenyl]-propionic acid methyl ester

Product 1

HCID 116926553-(4-{(S)-2-[2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-3-phenyl-propoxy}-phenyl)-propionic acid methyl esterYield 42%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

330 mg (0.5 mmol) of 3-[4-((S)-2-{2-methyl-4-[2,2,2-trifluoro-1-(4-methoxy-benzyloxy)-1-trifluoromethyl-ethyl]-phenoxy}-3-phenyl-propoxy)-phenyl]-propionic acid methyl ester in 10 mL of EtOAc were hydrogenated in the presence of 200 mg of 10% Pd/C. After removal of the catalyst and evaporation of the solvent, the residue was purified by column chromatography on silica gel with EtOAc/n-heptane 1:4 to yield 116 mg (42%) of 3-(4-{(S)-2-[2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-3-phenyl-propoxy}-phenyl)-propionic acid methyl ester as a light yellow oil, MS: 569 (M−H)−.

Workup

  1. customAfter removal of the catalyst and evaporation of the solvent
  2. customthe residue was purified by column chromatography on silica gel with EtOAc/n-heptane 1:4

Sources & evidence

ORD record
ord-a63a317737c94ac4ad97a47c5fdc8072
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

Loading…