Potassium Carbonate → HCID 91382246, compound

HRID 493471Notes

Reaction equation

HRID 493471 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:24][C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:28][O:27][C:25](=[O:26])[CH2:24][O:22][C:19]1[CH:20]=[CH:21][C:16]([C:13]2[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[CH:11][CH:12]=2)=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 57681613HCID 57681613, compound

Product 1

HCID 91382246HCID 91382246, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-{[(tert-butoxycarbonyl)amino]methyl}-4′-hydroxy-1,1′-biphenyl (2.05 g, 6.85 mmol), prepared in the previous step, methyl bromoacetate (648 μL, 6.85 mmol) and potassium carbonate (4.73 g, 34.2 mmol) in 50 mL of DMF was stirred under nitrogen at room temperature for 20 h (overnight). The reaction was partitioned between ethyl acetate and water. The organic layer was separated, extracted multiple times with water, dried (MgSO4) and the solvent removed under reduced pressure to give methyl[(4′-{[(tert-butoxycarbonyl)amino]methyl}[1,1′-biphenyl]-4-yl)oxy]acetate (2.46 g, 97%) as an off-white solid, mp 111-113° C. Elemental Analysis for C21H25NO5. Calc'd: C, 67.91; H, 6.78; N, 3.77 Found: C, 67.70; H, 6.74; N, 3.72

Workup

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

Sources & evidence

ORD record
ord-630f2b4ba40b42de805daf0fb40e7f22
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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