Sulfamide → Tert-butyl 4-sulfamoyl-1,4-diazepane-1-carboxylate

HRID 1024952Notes

Reaction equation

HRID 1024952 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[S:15](N)([NH2:18])(=[O:17])=[O:16]>O1CCOCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([S:15](=[O:17])(=[O:16])[NH2:18])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 67051265Tert-butyl 4-sulfamoyl-1,4-diazepane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 1,4-Diazepane-1-carboxylic acid tert-butyl ester (3.16 g) in dioxane (40 ml) was added sulfamide (4.0 g) and the reaction mixture was then heated at reflux for 18 h. The reaction mixture was then reduced in vacuo and the residue partitioned between EtOAc (100 ml) and H2O (100 ml). The organics were separated and the aqueous layer was re-extracted with EtOAc (2×100 ml). Organics were combined, dried (MgSO4) and reduced in vacuo to give the subtitle compound as a white solid. Yield: 4.27 g

Workup

  1. temperaturethe reaction mixture was then heated
  2. temperatureat reflux for 18 h
  3. customthe residue partitioned between EtOAc (100 ml) and H2O (100 ml)
  4. customThe organics were separated
  5. extractionthe aqueous layer was re-extracted with EtOAc (2×100 ml)
  6. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-31df86d366644453ba117502086ef8eb
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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