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Water → HCID 67119321, compound

HRID 2076694
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Reaction equation

HRID 2076694 reaction equation
[CH2:1]([O:4][C:5]1[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[C:14]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([CH2:36][C:37]([O:39][CH2:40][CH:41]=[CH2:42])=[O:38])=[C:32]([F:43])[CH:31]=3)=[CH:26][CH:25]=2)[C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:2]=[CH2:3].C(O[CH:49](OC(C)(C)C)[N:50]([CH3:52])[CH3:51])(C)(C)C.O>C1(C)C=CC=CC=1>[CH2:1]([O:4][C:5]1[C:17]([C:18]([F:20])([F:21])[F:19])=[CH:16][CH:15]=[C:14]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([C:37]([O:39][CH2:40][CH:41]=[CH2:42])=[O:38])=[CH:49][N:50]([CH3:52])[CH3:51])=[C:32]([F:43])[CH:31]=3)=[CH:26][CH:25]=2)[C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:2]=[CH2:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 67119033HCID 67119033, compound

Product 1

HCID 67119321HCID 67119321, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

tert-Butyl 2-(allyloxy)-6-{[(4′-{[(allyloxy)carbonyl]methyl}-3′-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (200 mg, 0.33 mmol) obtained in Example (11-6) was dissolved in toluene (3 ml) and N,N-dimethylformamide di-tert-butyl acetal (0.4 ml, 1.7 mmol) was added thereto, and the mixture was heated under reflux for 3 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate (three times), the organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1-1/1) to give tert-butyl 2-(allyloxy)-6-{[(4′-{1-[(allyloxy)carbonyl]-2-(dimethylamino)vinyl}-3′-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (141 mg, yield: 65%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate (three times)
  4. washthe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. customThe residue obtained
  7. customby removing the solvent under reduced pressure
  8. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=10/1-1/1)

Sources & evidence

ORD record
ord-9eee123ae2c547159096bec5d453c56f
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07923573B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes