Water → HCID 57704594, compound

HRID 2406047Notes

Reaction equation

HRID 2406047 reaction equation
[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([CH:25]([F:27])[F:26])[CH:19]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43].O>CN(C)C=O>[C:1]([O:5][C:6](=[O:28])[NH:7][C:8]1([CH2:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[C:20]([CH:25]([F:27])[F:26])[CH:19]=2)[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 81401-BromooctaneHCID 11430Potassium CarbonateHCID 57704618HCID 57704618, compound

Product 1

HCID 57704594HCID 57704594, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 30-4 (600 mg) was dissolved in N,N-dimethylformamide (10 ml), potassium carbonate (412 mg) and 1-bromooctane (0.311 ml) were added, and the mixture was stirred at room temperature for 2 hr. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-3:1) to give the object product (230 mg) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:1-3:1)

Sources & evidence

ORD record
ord-2d35bd01fda04a5b9bcae6c1603afe7f
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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