Potassium Carbonate → HCID 117689882, compound

HRID 928662Notes

Reaction equation

HRID 928662 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:19]=[C:20]([CH:35]=[CH:36][CH:37]=3)[C:21]([N:23]3[CH2:34][CH2:33][CH2:32][C@H:24]3[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:22])=[CH:12][CH:11]=2)[CH:5]=[C:6]([OH:9])[C:7]=1[F:8].C(=O)([O-])[O-].[K+].[K+].Br[CH2:45][C:46](=[O:48])[CH3:47]>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]3[CH:19]=[C:20]([CH:35]=[CH:36][CH:37]=3)[C:21]([N:23]3[CH2:34][CH2:33][CH2:32][C@H:24]3[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])=[O:22])=[CH:12][CH:11]=2)[CH:5]=[C:6]([O:9][CH2:45][C:46](=[O:48])[CH3:47])[C:7]=1[F:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 117689758HCID 117689758, compound

Product 1

HCID 117689882HCID 117689882, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (106 mg, 0.208 mmol) of Step 1 of Example 47 was dissolved in DMF (2 mL), and potassium carbonate (57.5 mg, 0.416 mmol) and bromoacetone (0.0192 mL, 0.229 mmol) were added thereto, and stirred at room temperature for 5 hours. The solvent was distilled away under reduced pressure. The resulting residue was diluted with ethyl acetate, washed with water and saturated brine, and then dried over anhydrous magnesium sulfate. The resultant was purified by silica gel chromatography to thus obtain the title compound.

Workup

  1. distillationThe solvent was distilled away under reduced pressure
  2. additionThe resulting residue was diluted with ethyl acetate
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe resultant was purified by silica gel chromatography

Sources & evidence

ORD record
ord-acdba5dbf78341aba4e89a4155bf9203
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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