Water → HCID 19348382, compound

HRID 1637260Notes

Reaction equation

HRID 1637260 reaction equation
[OH:1][C:2]1[C:10]2[NH:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:7]3[CH2:17][CH2:18][C:19](=[O:20])[C:5]([C:6]=23)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30].O>CS(C)=O>[CH3:32][O:31][C:29]([CH2:28][O:1][C:2]1[C:10]2[NH:9][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:7]3[CH2:17][CH2:18][C:19](=[O:20])[C:5]([C:6]=23)=[CH:4][CH:3]=1)=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 19348205HCID 19348205, compound

Product 1

HCID 19348382HCID 19348382, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A portion (1.09 g) of the compound obtained in Example 75 was dissolved in dimethylsulfoxide (20 ml) and to the solution were added potassium carbonate (1.14 g) and methyl bromoacetate (0.43 ml). The mixture was stirred for 1 hour at room temperature. After adding water, the reaction mixture was extracted three times with ethyl acetate. The organic layer was washed with water and saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was crystallized from ether to yield 1.18 g (85%) of the titled compound as a yellowish brown powder.

Workup

  1. extractionthe reaction mixture was extracted three times with ethyl acetate
  2. washThe organic layer was washed with water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was crystallized from ether

Sources & evidence

ORD record
ord-93f2ab6bbb5947859fb3c7e9a9800325
Source dataset
uspto-grants-2000_03
Patent number
US06040331

Reaction notes

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