Hydrochloric Acid → 4-[[3-Methyl-4-(4-trifluoromethyl-benzyloxy)phenyl]sulfanyl]-2-propylphenoxy-acetic acid

HRID 985043Notes

Reaction equation

HRID 985043 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([S:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[C:16]([CH3:32])[CH:15]=2)=[CH:9][C:8]=1[CH2:33][CH2:34][CH3:35])C.[Li+].[OH-].O.Cl>C1COCC1>[CH3:32][C:16]1[CH:15]=[C:14]([S:13][C:10]2[CH:11]=[CH:12][C:7]([O:6][CH2:5][C:4]([OH:36])=[O:3])=[C:8]([CH2:33][CH2:34][CH3:35])[CH:9]=2)[CH:19]=[CH:18][C:17]=1[O:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]([F:30])([F:31])[F:29])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 591291244-[[3-Methyl-4-(4-trifluoromethylbenzyloxy)phenyl]sulfanyl]-2-propylphenoxy-acetic acid ethyl ester

Product 1

HCID 103000564-[[3-Methyl-4-(4-trifluoromethyl-benzyloxy)phenyl]sulfanyl]-2-propylphenoxy-acetic acidYield 78%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 4.5 (32.7 g, 63.0 mmol) was dissolved in THF (250 mL). To the solution was added 4N LiOH (31.5 mL, 126 mmol) and the reaction was stirred at room temperature for 1 h, after which time water (31.5mL) was added, and the reaction mixture was stirred for 30 min. 2N HCl (70 mL) was then added to the reaction and the THF was removed in vacuo. The residue was diluted with hexane (250 mL) with stirring, and the deposited crystals were collected by filtration and recrystallized from EtOAc—hexane to provide 4 (24.12 g). MS APSI m/e: 489 (M−H). 1H NMR (400 MHz) (DMSO-d6) δ 12.90 (1H, brs); 7.76 (2H, d, J=8.2 Hz); 7.67 (2H, d, J=8.2 Hz); 7.20-7.05 (4H, m); 6.99 (1H, d, J=8.6 Hz); 6.81 (1H, d, J=8.4 Hz); 5.23 (2H, s); 4.68 (2H, s); 2.56-2.47 (2H, m); 2.18 (3H, s); 1.60-1.47 (2H, m); 0.85 (3H, t, J=7.4 Hz).

Workup

  1. stirringthe reaction mixture was stirred for 30 min
  2. customthe THF was removed in vacuo
  3. additionThe residue was diluted with hexane (250 mL)
  4. stirringwith stirring
  5. filtrationthe deposited crystals were collected by filtration
  6. customrecrystallized from EtOAc—hexane

Sources & evidence

ORD record
ord-8ba6a8a5a4e743b298f412cefc6ccf09
Source dataset
uspto-grants-2005_03
Patent number
US06869975B2

Reaction notes

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