Potassium Carbonate → HCID 69987925, compound

HRID 1634819Notes

Reaction equation

HRID 1634819 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[F:16])([CH3:4])([CH3:3])[CH3:2].Br[CH2:19][C:20]([O:22][CH3:23])=[O:21].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:23][O:22][C:20](=[O:21])[CH2:19][O:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:17])=[C:10]([F:16])[CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 53439114tert-Butyl [(2-fluoro-4-hydroxyphenyl)methyl]carbamate

Product 1

HCID 69987925HCID 69987925, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2-fluoro-4-hydroxy-benzyl)-carbamic acid t-butyl ester (0.47 g, 1.95 mmol), methyl bromoacetate (0.203 mL, 2.15 mmol) and potassium carbonate (0.431 g, 3.12 mmol) in DMF (5 mL) was stirred at ambient temperature overnight. The reaction mixture was partitioned with water and ethyl acetate. The organic phase was washed with water and dried (Na2SO4). Removal of solvent in vacuo afforded 0.59 g of the title compound.

Workup

  1. customThe reaction mixture was partitioned with water and ethyl acetate
  2. washThe organic phase was washed with water
  3. dry with materialdried (Na2SO4)
  4. customRemoval of solvent in vacuo

Sources & evidence

ORD record
ord-e3de0251e57342c9b81ebae4ac3581e8
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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