Potassium Carbonate → tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)glycinate

HRID 1497515Notes

Reaction equation

HRID 1497515 reaction equation
[C:1]([O:5][C:6]([NH:8][S:9]([NH:12][C:13]1[CH:14]=[C:15]([CH:32]=[CH:33][CH:34]=1)[CH2:16][N:17](C(=O)C(F)(F)F)[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([O:5][C:6]([NH:8][S:9]([NH:12][C:13]1[CH:14]=[C:15]([CH:32]=[CH:33][CH:34]=1)[CH2:16][NH:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])(=[O:10])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 90282078tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate

Product 1

HCID 90282027tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)glycinateYield 77.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate (2.19 g) were added a 50% aqueous methanol solution (43.9 mL) and potassium carbonate (1.19 g), followed by stirring at room temperature for 5 hours. The reaction mixture was concentrated under reduced pressure, and then the residue was dissolved in water, followed by neutralization with 1 M hydrochloric acid. The mixture was extracted with a mixed solvent of n-butanol and ethyl acetate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (methanol-chloroform) to obtain tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)glycinate (1.38 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. extractionThe mixture was extracted with a mixed solvent of n-butanol and ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (methanol-chloroform)

Sources & evidence

ORD record
ord-f0ce3e6cacef4a7ea1465bf4a5d642d9
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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