Potassium Carbonate → HCID 44404786, compound

HRID 1976468Notes

Reaction equation

HRID 1976468 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH:4]([NH:10][S:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:21][C:22]#[C:23][CH3:24])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH2:5][O:6][CH2:7][CH2:8]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:21]([O:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([N:10]2[CH2:8][CH2:7][O:6][CH2:5][CH:4]2[C:3]([O:2][CH3:1])=[O:25])(=[O:13])=[O:12])=[CH:15][CH:16]=1)[C:22]#[C:23][CH3:24]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 44404785HCID 44404785, compound

Product 1

HCID 44404786HCID 44404786, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2-bromo-ethoxy)-2-(4-[2-butynyloxy]-benzenesulfonyl-amino)propionic acid methyl ester (0.15 g, 0.35 mmol) dissolved in DMF (2 mL) and cooled in an ice bath was added potassium carbonate (0.16 g, 1.15 mmol) and the reaction was stirred at room temperature for 1 hour. After removing the solvent, the residue was extracted with ethyl acetate and water. The organic layer was washed with water and brine, dried over sodium sulfate, filtered, and concentrated to give 0.09 g of 4-([4-(2-butynyloxy)phenyl]sulfonyl}-morpholine-3-carboxylic acid, methyl ester as an oil. Yield ˜73.8%. Electrospray Mass Spec 354.2 (M+H)+.

Workup

  1. temperaturecooled in an ice bath
  2. customAfter removing the solvent
  3. extractionthe residue was extracted with ethyl acetate and water
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-928e7e23be374ea4bbf45f0683e29246
Source dataset
uspto-grants-2001_05
Patent number
US06225311B1

Reaction notes

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