Lithium Hydroxide → 3-{4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one

HRID 2263410Notes

Reaction equation

HRID 2263410 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[NH:35][C:34](=[O:36])[O:33][N:32]=1)[O:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:23][O:24]C(=O)C.[OH-].[Li+]>CO>[OH:24][CH2:23][C:9]1[N:10]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[CH:15][CH:14]=2)[S:12][C:8]=1[CH2:7][O:6][C:5]1[CH:28]=[CH:29][C:30]([C:31]2[NH:35][C:34](=[O:36])[O:33][N:32]=2)=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 136149964HCID 136149964, compound

Product 1

HCID 1361499483-{4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-oneYield 48.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 0.5 g of acetic acid 5-[3-methoxy-4-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenoxymethyl]-2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethyl ester in 5 mL of methanol at 0° C. was added 0.22 g of lithium hydroxide. The resulting solution was stirred for 45 minutes at 0° C. then it was allowed to warm up to room temperature. The solvent was partly removed under reduced pressure and ethyl acetate/1 molar aqueous solution of KH2PO4 was added. The organic layer was separated and the aqueous layer extracted three times with ethyl acetate. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. 40 mL of Ethyl acetate was added to the residue and, after stirring for 30 minutes, the resulting solid was collected by filtration to give 225 mg of 3-{4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-2-methoxy-phenyl}-4H-[1,2,4]oxadiazol-5-one as a beige solid.

Workup

  1. temperatureto warm up to room temperature
  2. customThe solvent was partly removed under reduced pressure and ethyl acetate/1 molar aqueous solution of KH2PO4
  3. additionwas added
  4. customThe organic layer was separated
  5. extractionthe aqueous layer extracted three times with ethyl acetate
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. addition40 mL of Ethyl acetate was added to the residue
  10. stirringafter stirring for 30 minutes
  11. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-e966cab009ce437c840aa9888b07dc42
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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