Ethyl(4-{4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)acetate → Ethyl (4-{3-[(4-fluorophenyl)sulphonyl]-4-hydroxybenzyl}-3,5-dimethylphenoxy)acetate

HRID 1836558Notes

Reaction equation

HRID 1836558 reaction equation
[CH2:1]([O:3][C:4](=[O:40])[CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21]CC3C=CC=CC=3)=[C:17]([S:29]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=3)(=[O:31])=[O:30])[CH:16]=2)=[C:9]([CH3:39])[CH:8]=1)[CH3:2]>C(O)C.[Pd]>[F:38][C:35]1[CH:34]=[CH:33][C:32]([S:29]([C:17]2[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=2[OH:21])[CH2:14][C:10]2[C:11]([CH3:13])=[CH:12][C:7]([O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:40])=[CH:8][C:9]=2[CH3:39])(=[O:31])=[O:30])=[CH:37][CH:36]=1

Participants

4

Reactant 1

HCID 23499607Ethyl(4-{4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)acetate

Product 1

HCID 86588309Ethyl (4-{3-[(4-fluorophenyl)sulphonyl]-4-hydroxybenzyl}-3,5-dimethylphenoxy)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

50 mg (0.09 mmol) of ethyl (4-{4-(benzyloxy)-3-[(4-fluorophenyl)sulphonyl]benzyl}-3,5-dimethylphenoxy)acetate (Example XI) are dissolved in 20 ml of ethanol. 10 mg of palladium on activated carbon (10%) are added, and the mixture is hydrogenated at 1013 mbar and room temperature for 2 hours. The reaction mixture is then filtered through Celite and the solvent is removed under reduced pressure. This gives 37 mg (86% of theory) of ethyl (4-{3-[(4-fluorophenyl)sulphonyl]-4-hydroxybenzyl}-3,5-di-methylphenoxy)acetate.

Workup

  1. filtrationThe reaction mixture is then filtered through Celite
  2. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-7d5048432f1942babfb1d6b99c2178f9
Source dataset
uspto-grants-2004_08
Patent number
US06777442B2

Reaction notes

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