Potassium Carbonate → HCID 68860367, compound

HRID 493509Notes

Reaction equation

HRID 493509 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].C(=O)([O-])[O-].[K+].[K+].[C:13]([O:17][C:18](=[O:33])[NH:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=2)=[CH:22][CH:21]=1)([CH3:16])([CH3:15])[CH3:14]>C1COCC1>[CH3:6][O:5][C:3](=[O:4])[CH2:2][O:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[CH:24]=[CH:25][C:20]([NH:19][C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:33])=[CH:21][CH:22]=2)=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 53218743tert-Butyl (4'-hydroxy[1,1'-biphenyl]-4-yl)carbamate

Product 1

HCID 68860367HCID 68860367, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl bromoacetate (128.5 mg, 0.84 mmol) potassium iodide (11.7 mg) and potassium carbonate (193.5 mg, 1.4 mmol) were added to a solution of (4′-hydroxy-biphenyl-4-yl)-carbamic acid tert-butyl ester (0.2 g, 0.70 mmol), prepared in the previous step, in 15 mL of THF and the reaction stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was partitioned between ethyl acetate and water. The aqueous layer was separated and extracted multiple times with ethyl acetate. The combined extracts were dried (Na2SO4) and the solvent removed under reduced pressure. Purification of the residue on silica gel using 20% ethyl acetate-hexane as the eluent gave (4′-tert-butoxycarbonylamino-biphenyl-4-yloxy)-acetic acid methyl ester (208 mg, 80%) as a white solid.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. customThe aqueous layer was separated
  4. extractionextracted multiple times with ethyl acetate
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. customthe solvent removed under reduced pressure
  7. customPurification of the residue on silica gel using 20% ethyl acetate-hexane as the eluent

Sources & evidence

ORD record
ord-71799ac908bc445b9c18d4146f8a87c1
Source dataset
uspto-grants-2009_05
Patent number
US07534894B2

Reaction notes

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