(1,1'-Biphenyl)-2-ol → [[4-(2,2-Dimethylpropyl)phenyl]methyl]heptylcarbamic acid[1,1'-biphenyl]-2-yl ester

HRID 1612651Notes

Reaction equation

HRID 1612651 reaction equation
Cl[C:2]([O:4][C:5](Cl)(Cl)Cl)=[O:3].[C:9]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2O)[CH:14]=[CH:13][CH:12]=[CH:11]C=1.C(N(CC)CC)C.[CH3:29][C:30]([CH3:48])([CH3:47])[CH2:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][NH:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])=[CH:34][CH:33]=1>C(Cl)Cl>[C:9]1([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:14]=[CH:13][CH:12]=[CH:11][C:5]=1[O:4][C:2](=[O:3])[N:39]([CH2:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][C:30]([CH3:29])([CH3:48])[CH3:47])=[CH:33][CH:34]=1)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46]

Participants

6

Reactant 4

HCID 7017(1,1'-Biphenyl)-2-olHCID 8471Triethylamine2×HCID 10426Diphosgene2×HCID 14995484HCID 14995484, compound

Product 1

HCID 54196462[[4-(2,2-Dimethylpropyl)phenyl]methyl]heptylcarbamic acid[1,1'-biphenyl]-2-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trichloromethyl chloroformate (2.1 mL, 17.4 mmol) is added dropwise over ten minutes under a nitrogen atmosphere to a solution of 2-phenylphenol (3.0 g, 17.6 mmol) in 50 mL of methylene chloride at ice bath temperature. After the addition of trichloromethyl chloroformate, triethylamine (2.5 mL, 17.9 mmol) is added dropwise over a ten minute period and the reaction mixture is stirred at ice bath temperature for 2.5 hours. A solution of N-[[4-(2,2-dimethylpropyl)phenyl]methyl]heptylamine (4.8 g, 17.4 mmol) and triethylamine (2.5 mL, 17.9 mmol) in methylene chloride (15 mL) is added at ice bath temperature over a thirty minute period. Then the ice bath is removed and the reaction mixture is stirred overnight. The reaction mixture is washed with 1N HCl, 5% NaHCO3, dried over MgSO4 and the solvent removed in vacuo to give, after purification by high pressure liquid chromatography (hexane-methylene chloride) the title compound as a light brown oil (2.37 g, 29% of theory), MS/me, 471 (M+).

Workup

  1. additionis added dropwise over a ten minute period
  2. customThen the ice bath is removed
  3. stirringthe reaction mixture is stirred overnight
  4. washThe reaction mixture is washed with 1N HCl, 5% NaHCO3
  5. dry with materialdried over MgSO4
  6. customthe solvent removed in vacuo
  7. customto give
  8. customafter purification by high pressure liquid chromatography (hexane-methylene chloride) the title compound as a light brown oil (2.37 g, 29% of theory), MS/me, 471 (M+)

Sources & evidence

ORD record
ord-c9e1ac209cb84f1d8fcf0d3cc4b4c68d
Source dataset
uspto-grants-1993_03
Patent number
US05190940

Reaction notes

Loading…