Hydrochloric Acid → GW 501516

HRID 1014073Notes

Reaction equation

HRID 1014073 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([S:15][CH2:16][C:17]2[S:21][C:20]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=3)=[N:19][C:18]=2[CH3:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[CH:14]=[C:13]([S:15][CH2:16][C:17]2[S:21][C:20]([C:22]3[CH:23]=[CH:24][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:26][CH:27]=3)=[N:19][C:18]=2[CH3:32])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 115258772-[2-Methyl-4-[[[4-methyl-2-[4-(trifluoromethyl)phenyl]-5-thiazolyl]methyl]thio]phenoxy]acetic acid ethyl ester

Product 1

HCID 9803963GW 501516Yield 98.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl {2-methyl-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole-5-yl sulfanyl]phenoxy}acetate obtained from Example 10 (5.0 g, 10.5 mmol) was dissolved in ethanol (200 ml) and 3N sodium hydroxide solution (35.0 ml) was added thereto. The reaction mixture was stirred for 30 minutes at room temperature. After completion of reaction, 2N HCl was added thereto for adjusting pH to be 2.0. Ethanol was evaporated by under reduced pressure and the reaction mixture was extracted with ethyl acetate and brine. Subsequently, the solvent was evaporated by under reduced pressure and the residue was purified by LH-20 column chromatography to thereby yield 4.71 g of the title compound (yield: 98.8%).

Workup

  1. additionwas added
  2. customEthanol was evaporated by under reduced pressure
  3. extractionthe reaction mixture was extracted with ethyl acetate and brine
  4. customSubsequently, the solvent was evaporated by under reduced pressure

Sources & evidence

ORD record
ord-1443f973f7eb4308886507bc2bfaf532
Source dataset
uspto-grants-2011_07
Patent number
US07982050B2

Reaction notes

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