Ethyl Acetate → HCID 67279025, compound

HRID 1694664Notes

Reaction equation

HRID 1694664 reaction equation
[C:1]([O:4][C@@H:5]([CH3:23])[C:6]([O:8][N:9]=[C:10]([NH2:22])[C:11]1[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([F:21])[CH:12]=1)=O)(=[O:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O1CCCC1>[C:1]([O:4][C@H:5]([C:6]1[O:8][N:9]=[C:10]([C:11]2[CH:12]=[C:13]([F:21])[CH:14]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:16]=2)[N:22]=1)[CH3:23])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 86622681HCID 86622681, compound

Product 1

HCID 67279025HCID 67279025, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-amino-2-[3-fluoro-5-(trifluoromethyl)phenyl]-1-azavinyl (2S)-2-acetyloxypropanoate (5.19 g, 15.43 mmol) in anhydrous tetrahydrofuran (20 ml) at 0° C. was added a solution of 1M tetrabutylammonium fluoride in tetrahydrofuran (3 ml) dropwise under nitrogen. The reaction mixture was stirred for 3 hours at 0° C., then poured into ethyl acetate (50 ml), washed with water (2×20 ml), brine (30 ml) and dried over sodium sulfate. Solvent was removed under reduced pressure, and the residue purified by flash chromatography, eluting with methylene chloride, to provide (1S)-1-{3-[5-fluoro-3-(trifluoromethyl)phenyl](1,2,4-oxadiazol-5-yl)}ethyl acetate, LCMS 319.1.

Workup

  1. washwashed with water (2×20 ml), brine (30 ml)
  2. dry with materialdried over sodium sulfate
  3. customSolvent was removed under reduced pressure
  4. customthe residue purified by flash chromatography
  5. washeluting with methylene chloride

Sources & evidence

ORD record
ord-d5e23709134b40a0b322786cdb645081
Source dataset
uspto-grants-2012_04
Patent number
US08158810B2

Reaction notes

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