Acetamide → HCID 59167767, compound

HRID 1039144Notes

Reaction equation

HRID 1039144 reaction equation
O=[C:2]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:3][O:4][C:5](=O)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13].C([NH2:26])(=O)C.B(F)(F)F.CCOCC>C([O-])(O)=O.[Na+]>[CH3:15][O:14][C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][C:5]1[O:4][CH:3]=[C:2]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:26]=1

Participants

5

Reactant 3

HCID 178AcetamideHCID 8000Boron trifluoride etherateHCID 59167744Octanedioic acid methyl ester 2-oxo-2-phenylethyl ester

Product 1

HCID 59167767HCID 59167767, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Heat a mixture of octanedioic acid methyl ester 2-oxo-2-phenylethyl ester (6.93 g, 22.6 mmol), acetamide (6.75 g, 114 mmol) and boron trifluoride diethyl etherate (3.0 mL, 23.7 mmol) at 135-140° C. under nitrogen for 4 hours. Cool the mixture, dilute with saturated NaHCO3 solution (100 mL), and extract with ethyl acetate (250 mL). Wash the organic extract with 100 mL of saturated aqueous sodium chloride (brine) and dry over sodium sulfate. Remove the solvent under reduced pressure and purify the residue by flash column chromatography on silica gel, eluting with hexanes/ethyl acetate (85:15), to provide 7-(4-phenyloxazol-2-yl)heptanoic acid methyl ester (5.7 g, 88%).

Workup

  1. temperatureHeat
  2. temperatureCool the mixture
  3. extractionextract with ethyl acetate (250 mL)
  4. washWash the
  5. extractionorganic extract with 100 mL of saturated aqueous sodium chloride (brine)
  6. dry with materialdry over sodium sulfate
  7. customRemove the solvent under reduced pressure
  8. custompurify the residue by flash column chromatography on silica gel
  9. washeluting with hexanes/ethyl acetate (85:15)

Sources & evidence

ORD record
ord-16877312d4d44af1bb2ba2e843db7d51
Source dataset
uspto-grants-2013_10
Patent number
US08552039B2

Reaction notes

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