Ammonia → HCID 11668393, compound

HRID 273181Notes

Reaction equation

HRID 273181 reaction equation
C([O:3][C:4]([C:6]1[O:10][N:9]=[C:8]([C@@H:11]2[CH2:15][C:14](=[O:16])[N:13]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([F:31])[CH:26]=4)=[CH:19][CH:18]=3)[CH2:12]2)[N:7]=1)=O)C.[NH3:32]>>[F:31][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][CH:28]=1)[CH2:24][O:23][C:20]1[CH:19]=[CH:18][C:17]([N:13]2[C:14](=[O:16])[CH2:15][C@@H:11]([C:8]3[N:7]=[C:6]([C:4]([NH2:32])=[O:3])[O:10][N:9]=3)[CH2:12]2)=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 11647545HCID 11647545, compound

Product 1

HCID 11668393HCID 11668393, compoundYield 44%

Conditions

Temperature
50 °C

Procedure

3-{(R)-1-[4-(3-Fluoro-benzyloxy)-phenyl]-5-oxo-pyrrolidin-3-yl}-[1,2,4]oxadiazole-5-carboxylic acid ethyl ester (0.110 g, 0.25 mmol) was dissolved in 3.5 ml of ammonia (2 M solution in methanol). The resulting mixture was stirred at 50° C. for half an hour. The mixture was cooled at 0° C. and a solid precipitated. The reaction mixture was filtrated and the solid washed with hexane and dried under vacuum. The residue was suspended in ethyl acetate and heated to reflux. Diethyl ether was added and the suspension cooled to 0° C. and filtrated to yield the title compound as a light brown solid (0.045 g, 44% of theory). MS (m/e)=397.4 (M+H)+.

Workup

  1. temperatureThe mixture was cooled at 0° C.
  2. customa solid precipitated
  3. filtrationThe reaction mixture was filtrated
  4. washthe solid washed with hexane
  5. customdried under vacuum
  6. temperatureheated to reflux
  7. additionDiethyl ether was added
  8. temperaturethe suspension cooled to 0° C.
  9. filtrationfiltrated

Sources & evidence

ORD record
ord-01480c5e6d0d4ec9b276988bbe5d90d8
Source dataset
uspto-grants-2008_11
Patent number
US07456210B2

Reaction notes

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