Sodium Hydroxide → HCID 136149956, compound

HRID 2263407Notes

Reaction equation

HRID 2263407 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[C:30]1[NH:34][C:33](=[O:35])[O:32][N:31]=1)[O:5][CH2:6][C:7]1[S:11][C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:9][C:8]=1[CH2:22][O:23]C(=O)C.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([O:5][CH2:6][C:7]2[S:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:20])([F:21])[F:19])=[CH:14][CH:13]=3)=[N:9][C:8]=2[CH2:22][OH:23])[CH:27]=[CH:28][C:29]=1[C:30]1[NH:34][C:33](=[O:35])[O:32][N:31]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 135446397HCID 135446397, compound

Product 1

HCID 136149956HCID 136149956, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
10 °C

Procedure

To a suspension of 150 mg of acetic acid 5-[3-fluoro-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 dropwise added 0.29 mL of a 1 molar aqueous solution of sodium hydroxide. After stirring for 15 minutes at 10° C., the reaction mixture was concentrated under reduced pressure. Ethyl acetate/a 1 molar aqueous solution of sodium hydrogenphosphate 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 to give 110 mg of 3-{2-fluoro-4-[4-hydroxymethyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-4H-[1,2,4]oxadiazol-5-one as a yellowish solid.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate/a 1 molar aqueous solution of sodium hydrogenphosphate was added
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted three times with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5df739de7cd4a86b4199ed7d4dd26a9
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

Loading…