Hydrochloric Acid → Ethyl {4-[benzyloxycarbonylmethyl-(4-fluorobenzoyl)amino]phenoxy)acetate

HRID 497058Notes

Reaction equation

HRID 497058 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[NH2:19][C:20]1[CH:32]=[CH:31][C:23]([O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:22][CH:21]=1.[F:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1.Cl>C(OCC)(=O)C.O.CN(C=O)C>[CH2:12]([O:11][C:9]([CH2:8][N:19]([C:38](=[O:39])[C:37]1[CH:41]=[CH:42][C:34]([F:33])=[CH:35][CH:36]=1)[C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:31][CH:32]=1)=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 678794-Fluorobenzoyl chlorideHCID 412616Ethyl 2-(4-aminophenoxy)acetate

Product 1

HCID 91495284Ethyl {4-[benzyloxycarbonylmethyl-(4-fluorobenzoyl)amino]phenoxy)acetate

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate and benzyl bromoacetate were added to DMF solution of ethyl (4-aminophenoxy)acetate and stirred under heating. After adding water and ethyl acetate to the reaction mixture, the organic layer was separated, washed and dried, and then the solvent was evaporated under a reduced pressure. Dichloromethane solution of the thus obtained crude product was mixed with TEA, 4-fluorobenzoyl chloride was added dropwise thereto under ice-cooling and then the reaction solution was stirred. After adding 1 M hydrochloric acid to the reaction solution, the organic layer was separated, washed and dried, and then the solvent was evaporated under a reduced pressure. By purifying the thus obtained crude product by SCG, ethyl {4-[benzyloxycarbonylmethyl-(4-fluorobenzoyl)amino]phenoxy}acetate (colorless oil) was obtained.

Workup

  1. temperatureunder heating
  2. customthe organic layer was separated
  3. washwashed
  4. customdried
  5. customthe solvent was evaporated under a reduced pressure
  6. customDichloromethane solution of the thus obtained crude product
  7. additionwas added dropwise
  8. temperatureunder ice-cooling
  9. stirringthe reaction solution was stirred
  10. customthe organic layer was separated
  11. washwashed
  12. customdried
  13. customthe solvent was evaporated under a reduced pressure
  14. customBy purifying the
  15. customthus obtained crude product by SCG

Sources & evidence

ORD record
ord-fc898232bff74f0d91c4f86377031b66
Source dataset
uspto-grants-2005_09
Patent number
US06949543B2

Reaction notes

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