Potassium Carbonate → HCID 67278867, compound

HRID 1694665Notes

Reaction equation

HRID 1694665 reaction equation
C([O:4][C@H:5]([C:7]1[O:11][N:10]=[C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)[N:8]=1)[CH3:6])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[F:18][C:16]1[CH:15]=[C:14]([C:19]([F:21])([F:20])[F:22])[CH:13]=[C:12]([C:9]2[N:8]=[C:7]([C@@H:5]([OH:4])[CH3:6])[O:11][N:10]=2)[CH:17]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 67279025HCID 67279025, compound

Product 1

HCID 67278867HCID 67278867, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (1S)-1-{3-[5-fluoro-3-(trifluoromethyl)phenyl](1,2,4-oxadiazol-5-yl)}ethyl acetate (900 mg, 2.83 mmol) in methanol (4 ml) at −15° C. was added an aqueous solution of potassium carbonate (10M, 10 ml). The mixture was stirred for 20 minutes, and the mixture allowed to warm to room temperature, stirring for 1 hour. The mixture was extracted with ethyl acetate (3×20 ml), and the combined organic phase washed with water (10 ml), brine (2×20 ml). Removal of the solvent under reduced pressure provided (1S)-1-{3-[5-fluoro-3-(trifluoromethyl)phenyl](1,2,4-oxadiazol-5-yl)}ethane-1-ol, which was crystallized from hexane to yield a white solid, LCMS 277.2.

Workup

  1. stirringstirring for 1 hour
  2. extractionThe mixture was extracted with ethyl acetate (3×20 ml)
  3. washthe combined organic phase washed with water (10 ml), brine (2×20 ml)
  4. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-5994e571e3eb4181b67780d4fdef358e
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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