Chlorosulfamic acid → HCID 15860250, compound

HRID 1417935Notes

Reaction equation

HRID 1417935 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:21]=[CH:20][C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13]([C:22](=[O:31])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=1.Cl[S:33]([NH2:36])(=[O:35])=[O:34].C(=O)(O)[O-].[Na+]>CN(C=O)C>[S:33]([O:3][C:4]1[CH:21]=[CH:20][C:19]2[C@@H:18]3[C@H:9]([C@H:10]4[C@@:14]([CH2:16][CH2:17]3)([CH3:15])[C:13]([C:22](=[O:31])[NH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:12][CH2:11]4)[CH2:8][CH2:7][C:6]=2[CH:5]=1)(=[O:35])(=[O:34])[NH2:36]

Participants

6

Reactant 4

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 54429803HCID 54429803, compound

Product 1

HCID 15860250HCID 15860250, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

About 29.6 mg of sodium hydride was added to a solution comprising about 250 mg of compound 4a in about 20 ml of anhydrous DMF at 0° C. under nitrogen. The solution was stirred for 30 minutes and about 1.22 g of chlorosulfonamide was slowly added in one portion. The solution was then stirred at room temperature for 24 hours. The mixture was poured into a cold saturated sodium bicarbonate solution and the resulting solution was extracted with methylene chloride (3×50 ml). The organic layer was separated, dried (Na2SO4) and concentrated under reduced pressure to give a light yellow oil (5a) (183 mg 61.2%).

Workup

  1. customat 0° C.
  2. stirringThe solution was then stirred at room temperature for 24 hours
  3. extractionthe resulting solution was extracted with methylene chloride (3×50 ml)
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-791ca14ff07c47929c2b3a55e549132e
Source dataset
uspto-grants-1999_03
Patent number
US05880115

Reaction notes

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