Hydrochloric Acid → HCID 86693755, compound

HRID 1469869Notes

Reaction equation

HRID 1469869 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][C@H:11]([C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[C:20]([F:31])[CH:19]=2)[N:14]=1)[CH3:12])(=O)C.Cl>CO>[F:31][C:20]1[CH:19]=[C:18]([C:15]2[N:14]=[C:13]([C@@H:11]([OH:10])[CH3:12])[O:17][N:16]=2)[CH:30]=[CH:29][C:21]=1[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 86693756HCID 86693756, compound

Product 1

HCID 86693755HCID 86693755, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Potassium carbonate (12.7 g, 91.6 mmol) was added to a methanol (360 mL) solution of the obtained tert-butyl 4-{5-[(1S)-1-acetoxyethyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate (32.1 g, 91.6 mmol) under ice cooling, and the mixture was stirred at the same temperature for 30 minutes. 2 N Hydrochloric acid was added to the reaction mixture at the same temperature until a pH value of 6.0 was obtained, and the solvent was distilled off under reduced pressure. Water was added to the resulting residue, and the mixture was subjected to extraction twice with ethyl acetate. The organic layer thus obtained was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was solidified by using hexane. Thus, the title compound (26.4 g, yield: 93%) was obtained.

Workup

  1. customwas obtained
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionWater was added to the resulting residue
  4. extractionthe mixture was subjected to extraction twice with ethyl acetate
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0e57285bbf6843d79bf4bdee05fbeb55
Source dataset
uspto-grants-2015_04
Patent number
US09006273B2

Reaction notes

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