Sulfamide → 1-(Aminosulfonyl)-N,N-dimethyl-D-prolinamide

HRID 729653Notes

Reaction equation

HRID 729653 reaction equation
[CH3:1][N:2]([CH3:10])[C:3](=[O:9])[C@H:4]1[CH2:8][CH2:7][CH2:6][NH:5]1.[S:11](N)([NH2:14])(=[O:13])=[O:12]>O1CCOCC1>[NH2:14][S:11]([N:5]1[CH2:6][CH2:7][CH2:8][C@@H:4]1[C:3]([N:2]([CH3:10])[CH3:1])=[O:9])(=[O:13])=[O:12]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 7021808(2R)-N,N-dimethylpyrrolidine-2-carboxamide

Product 1

HCID 667020511-(Aminosulfonyl)-N,N-dimethyl-D-prolinamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of the subtitle compound of step ii) (2.20 g) in dioxane (25 ml) was added sulfamide (7.20 g) and the mixture heated at reflux for 45 h. The reaction mixture was cooled and adsorbed on to silica gel and then purified by column chromatography (5% methanol/EtOAc) to afford the subtitle compound as an oil. Yield: 1.6 g.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 45 h
  3. temperatureThe reaction mixture was cooled
  4. custompurified by column chromatography (5% methanol/EtOAc)

Sources & evidence

ORD record
ord-13a8a446f25c4281bc402112d714c1d6
Source dataset
uspto-grants-2009_09
Patent number
US07582644B2

Reaction notes

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