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Water → HCID 67119111, compound

HRID 2076695
Notes
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Reaction equation

HRID 2076695 reaction equation
N1CCOCC1.C([O:10][C:11]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][CH:21]=[C:20]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([C:47]([O:49][CH2:50][CH:51]=[CH2:52])=[O:48])=[CH:43][N:44]([CH3:46])[CH3:45])=[C:38]([F:53])[CH:37]=3)=[CH:32][CH:31]=2)[C:12]=1[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])C=C.O>O1CCCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:10][C:11]1[C:23]([C:24]([F:26])([F:27])[F:25])=[CH:22][CH:21]=[C:20]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]3[CH:41]=[CH:40][C:39]([C:42]([C:47]([O:49][CH2:50][CH:51]=[CH2:52])=[O:48])=[CH:43][N:44]([CH3:45])[CH3:46])=[C:38]([F:53])[CH:37]=3)=[CH:32][CH:31]=2)[C:12]=1[C:13]([O:15][C:16]([CH3:17])([CH3:19])[CH3:18])=[O:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 8083MorpholineHCID 67119321HCID 67119321, compound

Product 1

HCID 67119111HCID 67119111, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst
HCID 8028
Tetrahydrofuran
Solvent

Procedure

Morpholine (0.02 ml, 0.23 mmol) and tetrakis(triphenylphosphine)palladium (0) (6 mg, 0.005 mmol) were successively added to a solution of tert-butyl 2-(allyloxy)-6-{[(4′-{1-[(allyloxy)carbonyl]-2-(dimethylamino)vinyl}-3′-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (67 mg, 0.10 mmol) obtained in Example (93-1) in tetrahydrofuran (1 ml), and the mixture was stirred at room temperature for 1 hour. After the reaction mixture was poured into water and the mixture was 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: n-hexane/ethyl acetate=10/1-1/>99) to give crude tert-butyl 2-hydroxy-6-{[(4′-{1-[(allyloxy)carbonyl]-2-(dimethylamino)vinyl}-3′-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoate (42 mg).

Workup

  1. extractionthe mixture was extracted 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: n-hexane/ethyl acetate=10/1-1/>99)

Sources & evidence

ORD record
ord-3e8bdbf2bfb04999b2f812eb2095e7e5
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