Potassium Carbonate → HCID 10658830, compound

HRID 275990Notes

Reaction equation

HRID 275990 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][O:10]C2CCCCO2)[CH:5]=[CH:4][C:3]=1[N:17]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])C(=O)C(F)(F)F.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][OH:10])[CH:5]=[CH:4][C:3]=1[NH:17][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 10526969HCID 10526969, compound

Product 1

HCID 10658830HCID 10658830, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl N-[2-chloro-4-[2-((RS)-tetrahydro-pyran-2-yloxy)ethyl]phenyl]-N-trifluoroacetylaminoacetate (830 mg) and p-toluenesulfonic acid monohydrate (80 mg) in ethanol (9.0 ml) was stirred for 2 hours at 40° C. To the reaction mixture was added potassium carbonate (314 mg), and the resulting mixture was heated under reflux for 5 hours with stirring. The insoluble material was filtered off, the filtrate was concentrated in vacuo, and the residue was dissolved in ethyl acetate. The solution was washed with a saturated aqueous sodium bicarbonate solution and brine, and dried over anhydrous magnesium sulfate, and the solvent was removed in vacuo. Purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1) gave ethyl N-[2-chloro-4-(2-hydroxyethyl)phenyl]aminoacetate (315 mg).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 5 hours
  3. filtrationThe insoluble material was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in ethyl acetate
  6. washThe solution was washed with a saturated aqueous sodium bicarbonate solution and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customthe solvent was removed in vacuo
  9. customPurification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-35889ec0550d4f4b9b3a035514cb5de5
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Reaction notes

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