Potassium Carbonate → HCID 66998781, compound

HRID 560268Notes

Reaction equation

HRID 560268 reaction equation
O=S(Cl)Cl.[CH2:5]([O:7][C:8](=[O:23])[CH:9]([NH:19][C:20](=[O:22])[CH3:21])[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)=O)[CH3:6].C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl>[CH2:5]([O:7][C:8]([C:9]1[N:19]=[C:20]([CH3:21])[O:22][C:10]=1[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1)=[O:23])[CH3:6]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 24386Thionyl Chloride2×HCID 66998524HCID 66998524, compound

Product 1

HCID 66998781HCID 66998781, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

At 0° C. SOCl2 (0.88 mmol) is added to a stirred solution of 2-acetylamino-3-(3-fluoro-phenyl)-3-oxo-propionic acid ethyl ester (0.63 mmol) in CHCl3 (0.38 mL). After 30 min the mixture is heated to reflux for 60 min. An additional portion of SOCl2 (0.16 mmol) is added and the mixture is heated to reflux for further 60 min. An aq. K2CO3 solution (1.0 M) is added, the layers are separated and the aq. layer is extracted twice with ether. The combined organic layers are washed with water, dried over MgSO4, filtered and concentrated in vacuo to give the desired ester which is used without further purification. LC-MS: tR=0.93 min; [M+H]+=250.3.

Workup

  1. customAt 0° C
  2. temperatureAfter 30 min the mixture is heated
  3. temperatureto reflux for 60 min
  4. temperaturethe mixture is heated
  5. temperatureto reflux for further 60 min
  6. customthe layers are separated
  7. extractionthe aq. layer is extracted twice with ether
  8. washThe combined organic layers are washed with water
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1a812325331148c0a1983e48fe6450b1
Source dataset
uspto-grants-2011_11
Patent number
US08063099B2

Reaction notes

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