HCID 10379035, compound → HCID 10061571, compound

HRID 2371416Notes

Reaction equation

HRID 2371416 reaction equation
CSC.B.O=[C:6]1[CH2:11][S:10](=[O:13])(=[O:12])[C:9]2[S:14][C:15]([S:17](=[O:20])(=[O:19])[NH2:18])=[CH:16][C:8]=2[NH:7]1>C1COCC1>[O:13]=[S:10]1(=[O:12])[CH2:11][CH2:6][NH:7][C:8]2[CH:16]=[C:15]([S:17](=[O:19])(=[O:20])[NH2:18])[S:14][C:9]1=2

Participants

4

Reactant 2

HCID 10379035HCID 10379035, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 10061571HCID 10061571, compoundYield 15.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Borane dimethylsulfide in THF (4.4 ml, 10M, 44 mmol) was added slowly to a solution of 2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazine (2.5 g, 8.9 mmol) in THF (10 ml) at 0° C. The reaction mixture was warmed to ambient temperature and stirred for an addidition hour. Excess borane was destroyed by the addition of 6N HCl and borane adducts were cleaved by heating at reflux for one hr. The solvent was removed and the residue was partitioned between water and ethyl acetate. The organic phase was washed with water and brine then dried over sodium sulfate. After filtration and evaporation of the solvent, the residue was chromatographed over silica gel with CHCl3 /MeOH/NH4OH (80:20:2). Fractions containing the desired product were combined, evaporated and the solid residue was triturated with ethyl acetate to yield 0.36 g 2,3-dihydro-4,4-dioxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazine, mp 250°-252° C.

Workup

  1. customExcess borane was destroyed by the addition of 6N HCl and borane adducts
  2. temperatureby heating
  3. temperatureat reflux for one hr
  4. customThe solvent was removed
  5. customthe residue was partitioned between water and ethyl acetate
  6. washThe organic phase was washed with water and brine
  7. dry with materialthen dried over sodium sulfate
  8. filtrationAfter filtration and evaporation of the solvent
  9. customthe residue was chromatographed over silica gel with CHCl3 /MeOH/NH4OH (80:20:2)
  10. additionFractions containing the desired product
  11. customevaporated
  12. customthe solid residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-ae5844734ec248018bf31406b06fc15e
Source dataset
uspto-grants-1992_03
Patent number
US05093332

Reaction notes

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