Water → Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({4'-[(methoxycarbonyl)methyl]-2'-nitro-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate

HRID 2076705Notes

Reaction equation

HRID 2076705 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=2[N+:25]([O-:27])=[O:26])=[CH:10][CH:9]=1.Br[CH2:29][C:30]1[C:35]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[C:34]([O:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])[C:33]([C:51]([F:54])([F:53])[F:52])=[CH:32][CH:31]=1.O>CC(C)=O>[C:47]([O:46][C:44]([O:43][C:34]1[C:33]([C:51]([F:52])([F:53])[F:54])=[CH:32][CH:31]=[C:30]([CH2:29][O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][C:15]=3[N+:25]([O-:27])=[O:26])=[CH:10][CH:9]=2)[C:35]=1[C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[O:45])([CH3:48])([CH3:49])[CH3:50]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67119234Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoateHCID 86088130Methyl (4'-hydroxy-2-nitro-1,1'-biphenyl-4-yl)acetate

Product 1

HCID 67119306Tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({4'-[(methoxycarbonyl)methyl]-2'-nitro-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

Potassium carbonate (147 mg, 1.06 mmol) was added to a solution of methyl (4′-hydroxy-2-nitro-1,1′-biphenyl-4-yl)acetate (203 mg, 0.71 mmol) obtained in Example (37-1) and tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (330 mg, 0.781 mmol) obtained in Example (28-5) in acetone (15 ml), and the mixture was stirred at 70° C. for 8 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was subjected to silica gel column chromatography (eluting solvent: hexane/ethyl acetate=4/1) to give crude tert-butyl 2-[(tert-butoxycarbonyl)oxy]-6-[({4′-[(methoxycarbonyl)methyl]-2′-nitro-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with water
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
  4. customThe residue obtained
  5. customby removing the solvent under reduced pressure
  6. washwas subjected to silica gel column chromatography (eluting solvent: hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-712de128d4994735aad882b5fa2d1d43
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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