Potassium Carbonate → HCID 57681616, compound

HRID 493475Notes

Reaction equation

HRID 493475 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[OH:8].Br[CH2:25][C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:29][O:28][C:26](=[O:27])[CH2:25][O:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[CH:10]=[CH:11][C:12]([CH2:15][NH:16][C:17]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:23])=[CH:13][CH:14]=2)=[CH:3][C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 57681614HCID 57681614, compound

Product 1

HCID 57681616HCID 57681616, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl (3′-bromo-4′-hydroxy[1,1′-biphenyl]-4-yl)methylcarbamate (1.50 g, 3.97 mmol), prepared in the previous step, methyl bromoacetate (376 μL, 3.97 mmol) and potassium carbonate (2.74 g, 19.86 mmol) in 50 mL of DMF was stirred under nitrogen at room temperature for 19 h (overnight). The reaction was partitioned between methylene chloride and water. The organic layer was separated, extracted five times with water, dried (MgSO4) and the solvent removed under reduced pressure to give methyl[(3-bromo-4′-{[(tert-butoxycarbonyl)amino]methyl}[1,1′-biphenyl]-4-yl)oxy]acetate (1.67 g, 93%) as a white solid, mp 96-98° C. Elemental Analysis for C21H24BrNO5. Calc'd: C, 56.01; H, 5.37; N, 3.11. Found: C, 55.47; H, 5.40; N, 3.00

Workup

  1. customThe reaction was partitioned between methylene chloride and water
  2. customThe organic layer was separated
  3. extractionextracted five times with water
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-f62eaf7f3ad646449ca1645d1f1d6f78
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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