Water → HCID 86605175, compound

HRID 1793938Notes

Reaction equation

HRID 1793938 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][C:12]=1[NH:20][S:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:23])=[O:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[CH2:36](I)[CH3:37].O>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][C:12]=1[N:20]([CH2:36][CH3:37])[S:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])(=[O:23])=[O:22])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 86605176HCID 86605176, compound

Product 1

HCID 86605175HCID 86605175, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 0.387 g of ethyl [[2-(2-tert-butoxycarbonylaminoethyl)-5-isopropylphenyl]sulfamoyl]acetate in 5 mL of N,N-dimethylformamide were added 0.131 g of potassium carbonate and 0.169 g of ethyl iodide at room temperature, and the mixture was stirred at the same temperature for 2 hours. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 0.342 g of ethyl [[2-(2-tert-butoxycarbonylaminoethyl)-5-isopropylphenyl](ethyl)sulfamoyl]acetate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-488b7d6d51314d338a452ff518e1154d
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

Loading…