Hydrochloric Acid → GW-0742

HRID 6845Notes

Reaction equation

HRID 6845 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])=[C:24]([F:32])[CH:23]=3)=[N:19][C:18]=2[CH3:33])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([O:8]CC)=[O:7].[Li+].[OH-].O.Cl>C1COCC1>[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:29])[F:30])=[C:24]([F:32])[CH:23]=3)=[N:19][C:18]=2[CH3:33])[CH:12]=[CH:11][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 9913867Ethyl 2-[4-[[[2-[3-fluoro-4-(trifluoromethyl)phenyl]-4-methyl-5-thiazolyl]methyl]thio]-2-methylphenoxy]acetate

Product 1

HCID 9934458GW-0742

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 2a (1 mmol) in THF (10 mL) was treated with 1N LiOH in water (2 mL, 2 mmol), and stirred 16 h at room temperature (when reactions were slow, the temperature was elevated to 50° C.). The solution was neutralized with 1N HCl (2 mL, 2 mmol) and the organic solvent evaporated to afford an aqueous solution with an insoluble product. If the insoluble was a solid, it was filtered and dried to afford the final product. If the insoluble was an oil, it was extracted with EtOAc (30 mL). The organic solution was separated, washed with water (2×30 mL), dried, filtered, and evaporated to afford the final product.

Workup

  1. customwas elevated to 50° C.
  2. customthe organic solvent evaporated
  3. customto afford an aqueous solution with an insoluble product
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-c2bfe43fcebe4adc8c2978aa82da026e
Source dataset
uspto-grants-2006_08
Patent number
US07084161B2

Reaction notes

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