Ethyl bromoacetate → HCID 10526969, compound

HRID 275989Notes

Reaction equation

HRID 275989 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH:12]=[CH:11][C:3]=1[NH:4][C:5](=[O:10])[C:6]([F:9])([F:8])[F:7].[H-].[Na+].Br[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(OCC)(=O)C>CN(C)C=O>[Cl:1][C:2]1[CH:14]=[C:13]([CH2:15][CH2:16][O:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][O:19]2)[CH:12]=[CH:11][C:3]=1[N:4]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:5](=[O:10])[C:6]([F:8])([F:7])[F:9]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 10712935HCID 10712935, compound

Product 1

HCID 10526969HCID 10526969, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 2′-chloro-4′-[2-((RS)-tetra-hydropyran-2-yloxy)ethyl]-2,2,2-trifluoroacetanilide (352 mg) in N,N-dimethylformamide (3 ml) was added sodium hydride (48 mg) under ice-cooling, and the mixture was stirred for 30 minutes at room temperature. Ethyl bromoacetate (133 μl) was added to the reaction mixture, and the mixture was stirred for 16 hours. Ethyl acetate was added to the reaction mixture, and the resulting mixture was washed with brine and dried over anhydrous magnesium sulfate. After the solvent was removed in vacuo, purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=2/1) gave ethyl N-[2-chloro-4-[2-((RS)-tetrahydropyran-2-yloxy)ethyl]phenyl]-N-trifluoroacetylamino-acetate (250 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 16 hours
  3. washthe resulting mixture was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter the solvent was removed in vacuo, purification of the residue by medium pressure liquid column chromatography on silica gel (eluent: hexane/diethyl ether=2/1)

Sources & evidence

ORD record
ord-3039eb2d0b434dd2bd5e566afa509e3e
Source dataset
uspto-grants-2002_03
Patent number
US06353025B1

Reaction notes

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