Hydrochloric Acid → HCID 19106480, compound

HRID 1197430Notes

Reaction equation

HRID 1197430 reaction equation
[C:1]([N:4]1[CH2:10][C:9]2[CH:11]=[C:12]([S:14](=[O:17])(=[O:16])[NH2:15])[S:13][C:8]=2[S:7](=[O:19])(=[O:18])[CH2:6][CH2:5]1)(=O)[CH3:2].B(F)(F)F.CCOCC.CO.[ClH:31]>C1COCC1>[ClH:31].[CH2:1]([N:4]1[CH2:10][C:9]2[CH:11]=[C:12]([S:14](=[O:16])(=[O:17])[NH2:15])[S:13][C:8]=2[S:7](=[O:18])(=[O:19])[CH2:6][CH2:5]1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 8000Boron trifluoride etherateHCID 19106465HCID 19106465, compound

Product 1

HCID 19106480HCID 19106480, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Acetyl-7-sulfamoyl-2,3,4,5-tetrahydrothieno[3,2-f]-1,4-thiazepin-1,1-dioxide (200 mg, 0.62 mmol) was dissolved in dry THF (10 mL), boron trifluoride etherate (0.15 mL) was added and the reaction mixture was refluxed for 0.5 hour. Borane dimethyl sulfide complex (0.7 mL) was added and the reaction mixture was refluxed for 1 hour. The reaction mixture was cooled and methanol and isopropanolic HCl were added. This solution was refluxed for 0.5 hours and the solvents removed. The residue was chromatographed on silica gel eluting with 10% methanol-methylene chloride. Appropriate fractions were combined, isopropanolic HCl added and the solvents evaporated to give 110 mg (27%) of the title compound as its hydrochloride salt. Recrystallization from isopropanol afforded analytically pure material as the hydrochloride salt solvated with one equivalent of isopropanol.

Workup

  1. temperaturethe reaction mixture was refluxed for 0.5 hour
  2. additionBorane dimethyl sulfide complex (0.7 mL) was added
  3. temperaturethe reaction mixture was refluxed for 1 hour
  4. temperatureThe reaction mixture was cooled
  5. temperatureThis solution was refluxed for 0.5 hours
  6. customthe solvents removed
  7. customThe residue was chromatographed on silica gel eluting with 10% methanol-methylene chloride
  8. additionisopropanolic HCl added
  9. customthe solvents evaporated

Sources & evidence

ORD record
ord-2935942700bc4cbaa254aa1a19c6f93e
Source dataset
uspto-grants-1994_01
Patent number
US05276025

Reaction notes

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