Dimethylsulphamoyl chloride → HCID 53685931, compound

HRID 1584416Notes

Reaction equation

HRID 1584416 reaction equation
[NH2:1][C@@H:2]([CH2:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[C:3]([NH:5][O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:4].[CH3:28][N:29]([CH3:34])[S:30](Cl)(=[O:32])=[O:31]>C(Cl)Cl.N1C=CC=CC=1>[C:7]([O:6][NH:5][C:3](=[O:4])[C@@H:2]([NH:1][S:30]([N:29]([CH3:34])[CH3:28])(=[O:32])=[O:31])[CH2:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:19][CH:20]=1)(=[O:13])=[O:14])([CH3:8])([CH3:9])[CH3:10]

Participants

5

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 54213503HCID 54213503, compound

Product 1

HCID 53685931HCID 53685931, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-amino-N-tert-butoxy-3-(4-phenoxyphenylsulfonyl)-propionamide (1.5 g) in methylene chloride (20 ml) and pyridine (1.2 ml) was added dimethylsulfamoyl chloride (1 ml), and the mixture stirred overnight at room temperature. The mixture was partitioned between methylene chloride and water, and after the organic layer was dried over magnesium sulfate, solvent was removed under reduced pressure. The residue was chromatographed on silica gel, eluting with 0-45% ethyl acetate/hexane, to give (R)-N-tert-butoxy-2-dimethylaminosulfonamido-3-(4-phenoxyphenylsulfonyl)-propionamide (1.6 g).

Workup

  1. customThe mixture was partitioned between methylene chloride and water
  2. dry with materialafter the organic layer was dried over magnesium sulfate, solvent
  3. customwas removed under reduced pressure
  4. customThe residue was chromatographed on silica gel
  5. washeluting with 0-45% ethyl acetate/hexane

Sources & evidence

ORD record
ord-e12a3fc2e69746d2bdbd68f0aab4c742
Source dataset
uspto-grants-1999_08
Patent number
US05932595

Reaction notes

Loading…