Acetic Anhydride → HCID 178471878, compound

HRID 358878Notes

Reaction equation

HRID 358878 reaction equation
C(OC(=O)C)(=O)C.[CH:8]([O-:13])([O-])[O:9][CH2:10][CH3:11].[CH3:14][O:15][C:16]1[C:17]([F:32])=[C:18]([CH:27]=[C:28]([F:31])[C:29]=1[F:30])[C:19]([CH2:21][C:22](OCC)=O)=[O:20].[CH:33]1([NH2:36])[CH2:35][CH2:34]1>C(Cl)Cl>[CH:33]1([NH:36][CH:22]=[C:21]([C:19](=[O:20])[C:18]2[CH:27]=[C:28]([F:31])[C:29]([F:30])=[C:16]([O:15][CH3:14])[C:17]=2[F:32])[C:8]([O:9][CH2:10][CH3:11])=[O:13])[CH2:35][CH2:34]1

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 69828CyclopropylamineHCID 10588473Ethyl 3-oxo-3-(2,4,5-trifluoro-3-methoxyphenyl)propanoateHCID 53630039Ethylorthoformate

Product 1

HCID 178471878HCID 178471878, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.5 ml of acetic anhydride and 1.1 ml of ethyl orthoformate were added to 1.40 g (0.005 mole) of ethyl 3-methoxy-2,4,5-trifluorobenzoylacetate (XXIX) [prepared as described in Step (E9) above], and the mixture was heated under reflux for 1 hour and then concentrated by evaporation under reduced pressure. 0.38 g (0.006 mole) of cyclopropylamine was added dropwise, whilst ice-cooling and stirring, to a solution of the residue in 10 ml of methylene chloride, and the mixture was stirred for a further 30 minutes. The solvent was then removed by evaporation under reduced pressure from the reaction mixture, and the residue was subjected to silica gel column chromatography eluted with a 9:1 by volume mixture of toluene and ethyl acetate, to afford 1.23 g of ethyl 3-cyclopropylamino-2-(3-methoxy-2,4,5-trifluorobenzoyl)acrylate (XXXI) as a pale brown oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. concentrationconcentrated by evaporation under reduced pressure
  4. temperaturecooling
  5. customThe solvent was then removed by evaporation under reduced pressure from the reaction mixture
  6. washeluted with a 9:1 by volume mixture of toluene and ethyl acetate

Sources & evidence

ORD record
ord-51b9740b049b4c07b187ce595627ede1
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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