Water → HCID 67119179, compound

HRID 2076650Notes

Reaction equation

HRID 2076650 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([C:10]1[CH:15]=[C:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:13]=[CH:12][C:11]=1[C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)(=[O:9])[CH3:8].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>CN(C)C=O>[C:7]([C:10]1[CH:15]=[C:14]([CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:13]=[CH:12][C:11]=1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:29][C:30]2[C:35]([C:36]([O:38][C:39]([CH3:40])([CH3:41])[CH3:42])=[O:37])=[C:34]([O:43][C:44]([O:46][C:47]([CH3:49])([CH3:48])[CH3:50])=[O:45])[C:33]([C:51]([F:52])([F:53])[F:54])=[CH:32][CH:31]=2)=[CH:23][CH:22]=1)(=[O:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 67119234Tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoateHCID 86241523HCID 86241523, compound

Product 1

HCID 67119179HCID 67119179, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (209 mg, 0.644 mmol) was added to a solution of methyl (2-acetyl-4′-hydroxy-1,1′-biphenyl-4-yl)acetate (122 mg, 0.429 mmol) obtained in Example (40-1) and tert-butyl 6-(bromomethyl)-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (181 mg, 0.429 mmol) obtained in Example (28-5) in N,N-dimethylformamide (4 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water and extracted with ethyl acetate (three times). After the organic layer was successively washed with water (three times) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate, it was concentrated under reduced pressure. The obtained residue was purified by silica gel preparative thin layer chromatography (developing solvent: hexane/ethyl acetate=3/1) to give tert-butyl 6-[({2′-acetyl-4′-[(methoxycarbonyl)methyl]-1,1′-biphenyl-4-yl}oxy)methyl]-2-[(tert-butoxycarbonyl)oxy]-3-(trifluoromethyl)benzoate (93 mg, yield: 34%).

Workup

  1. extractionextracted with ethyl acetate (three times)
  2. washAfter the organic layer was successively washed with water (three times)
  3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate, it
  4. concentrationwas concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel preparative thin layer chromatography (developing solvent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-0309cc71bfc24e66bdc079eb4a870ed9
Source dataset
uspto-grants-2011_04
Patent number
US07923573B2

Reaction notes

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