Water → HCID 66758388, compound

HRID 1643250Notes

Reaction equation

HRID 1643250 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([OH:15])=[CH:10][C:9]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][CH3:26].O>CN(C=O)C>[C:1]([O:5][C:6](=[O:17])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([O:15][CH2:25][CH3:26])=[CH:10][C:9]=1[CH3:16])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6332Ethyl BromideHCID 11430Potassium Carbonate2×HCID 106099214-hydroxy-2,5-dimethyl-phenyl-carbamic acid tert-butyl ester

Product 1

HCID 66758388HCID 66758388, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 35 (4 mmol, 948 mg) in 5 mL DMF, potassium carbonate (K2CO3, 8 mmol, 1.1 g) and bromoethane (4.8 mmol, 523 mg) were added. The reaction was stirred overnight at 60° C. Water (2 mL) was added to dissolve the unreacted potassium carbonate, and the reaction mixture was then extracted with ethyl acetate (3×10 mL). The organic layers were combined and dried over Na2SO4. After removal of the solvent, the crude product was purified by using flash chromatography (0-30% ethyl acetate/hexane) to give the title product 36 (90% yield).

Workup

  1. extractionthe reaction mixture was then extracted with ethyl acetate (3×10 mL)
  2. dry with materialdried over Na2SO4
  3. customAfter removal of the solvent
  4. customthe crude product was purified

Sources & evidence

ORD record
ord-19564cffbf6942719aa25d66c3b2904d
Source dataset
uspto-grants-2012_02
Patent number
US08119680B2

Reaction notes

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