Potassium Carbonate → HCID 19980210, compound

HRID 1461236Notes

Reaction equation

HRID 1461236 reaction equation
C[C:2]1[C:7](=[O:8])[C:6]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:5][N:4]([OH:19])[C:3]=1[CH2:20][OH:21].[C:22](=O)([O-])[O-].[K+].[K+].[C:28]1([CH:34](Br)[C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C)C=O>[CH3:22][C:5]1[N:4]([O:19][CH:34]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:3]([CH2:20][OH:21])=[CH:2][C:7](=[O:8])[C:6]=1[O:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 236603BromodiphenylmethaneHCID 19980219HCID 19980219, compound

Product 1

HCID 19980210HCID 19980210, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1 g of 6 methyl-5-p-methoxybenzyloxy-2-hydroxymethyl-1-hydroxy-4-pyridone in 60 ml of dimethylformamide were successively added 710 mg of potassium carbonate and 1.3 g of diphenylmethyl bromide. The mixture was stirred at room temperature for 17 hours. After completion of the reaction, the reaction liquid was concentrated and the concentrate was added to 20 ml of water and 40 ml of dichloromethane. The organic phase was washed with 20 ml of water. After drying over anhydrous magnesium sulfate, the organic phase was concentrated under reduced pressure. The concentrate was separated and purified by flash column chromatography (eluting solution; chloroform: methanol=20:1) using Wako Gel C-300 (100 g) to give 1.35 g of the title compound.

Workup

  1. customAfter completion of the reaction
  2. customthe reaction liquid
  3. concentrationwas concentrated
  4. additionthe concentrate was added to 20 ml of water and 40 ml of dichloromethane
  5. washThe organic phase was washed with 20 ml of water
  6. dry with materialAfter drying over anhydrous magnesium sulfate
  7. concentrationthe organic phase was concentrated under reduced pressure
  8. customThe concentrate was separated
  9. custompurified by flash column chromatography (eluting solution; chloroform: methanol=20:1)

Sources & evidence

ORD record
ord-e9ecff326d314a6884fb7f11e89c299e
Source dataset
uspto-grants-1991_12
Patent number
US05075299

Reaction notes

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