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

HRID 1497514Notes

Reaction equation

HRID 1497514 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C(N(CC)CC)C.Cl[S:32]([NH:35][C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])(=[O:34])=[O:33].O>ClCCl>[C:38]([O:37][C:36]([NH:35][S:32]([NH:1][C:2]1[CH:3]=[C:4]([CH:21]=[CH:22][CH:23]=1)[CH2:5][N:6]([C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])[CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])(=[O:34])=[O:33])=[O:42])([CH3:41])([CH3:39])[CH3:40]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 15677406tert-butyl N-(chlorosulfonyl)carbamateHCID 90282000tert-butyl N-(3-aminobenzyl)-N-(trifluoroacetyl)glycinate

Product 1

HCID 90282078tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinateYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl N-(3-aminobenzyl)-N-(trifluoroacetyl)glycinate (1.95 g) and triethylamine (0.981 mL) in dichloromethane (19.5 mL) was added a solution of tert-butyl (chlorosulfonyl)carbamate (1.52 g) in dichloromethane (10.0 mL) under ice-cooling, followed by stirring at room temperature for 3 hours. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added ethyl acetate, and n-hexane was added thereto. The precipitated solid was collected by filtration to obtain tert-butyl N-(3-{[(tert-butoxycarbonyl)sulfamoyl]amino}benzyl)-N-(trifluoroacetyl)glycinate (2.19 g).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous sodium hydrogen carbonate solution
  4. dry with materiala saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added ethyl acetate, and n-hexane
  7. additionwas added
  8. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-ab444a29f427438982f56848eaefccda
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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