Hydrochloric Acid → HCID 19106460, compound

HRID 1197438Notes

Reaction equation

HRID 1197438 reaction equation
[C:1]([N:6]1[CH:12]([CH3:13])[C:11]2[CH:14]=[C:15]([S:17](=[O:20])(=[O:19])[NH2:18])[S:16][C:10]=2[S:9](=[O:22])(=[O:21])[CH2:8][CH2:7]1)(=O)[CH:2]([CH3:4])[CH3:3].B.C1COCC1.Cl.O>O1CCCC1>[CH2:1]([N:6]1[CH:12]([CH3:13])[C:11]2[CH:14]=[C:15]([S:17](=[O:20])(=[O:19])[NH2:18])[S:16][C:10]=2[S:9](=[O:21])(=[O:22])[CH2:8][CH2:7]1)[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 19106454HCID 19106454, compound

Product 1

HCID 19106460HCID 19106460, compoundYield 65.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-isobutyryl-5(R,S)-methyl-7-sulfamoyl-2,3,4,5-tetrahydrothieno[3.2-f]-1,4-thiazepine-1,1-dioxide (1.009 g, 2.75 mmol) in dry tetrahydrofuran (30 mL), under an inert atmosphere was added 1M borane·THF (9 mL, 9.0 mmol) and the reaction mixture was refluxed for three hours. Concentrated HCl and water were then added to the cooled reaction mixture. After refluxing this mixture for 0.5 hours, the solvent was removed, the residue was made basic with NaHCO3 and the product was extracted into ethyl acetate. The extract was dried (Na2SO4), filtered and the solvent evaporated. Trituration of the residue with diethyl ether and n-butyl chloride gave 637 mg (65%) of crystalline product. Recrystallization of the solid from diethyl ether twice afforded analytically pure title compound (446 mg), mp 125°-127° C.

Workup

  1. temperaturethe reaction mixture was refluxed for three hours
  2. temperatureAfter refluxing this mixture for 0.5 hours
  3. customthe solvent was removed
  4. extractionthe product was extracted into ethyl acetate
  5. dry with materialThe extract was dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-8a680c85eb5243fb8eef67e966e03c7d
Source dataset
uspto-grants-1994_01
Patent number
US05276025

Reaction notes

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