Methanol → HCID 10335685, compound

HRID 2371419Notes

Reaction equation

HRID 2371419 reaction equation
B.CSC.O=[C:6]1[CH:11]([CH2:12][C:13](O)=[O:14])[S:10](=[O:17])(=[O:16])[C:9]2[S:18][C:19]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:20][C:8]=2[NH:7]1.CO>C(COC)OC>[OH:14][CH2:13][CH2:12][CH:11]1[S:10](=[O:16])(=[O:17])[C:9]2[S:18][C:19]([S:21](=[O:23])(=[O:24])[NH2:22])=[CH:20][C:8]=2[NH:7][CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 10359893HCID 10359893, compoundHCID 12423031(Dimethyl sulfide)trihydroboron

Product 1

HCID 10335685HCID 10335685, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Borane-dimethylsulfide (9.5 ml, 10M, 95 mmol) was added to a solution of (2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno-[2,3-b][1,4]thiazin-3-yl)acetic acid (3.25 g, 9.5 mmol) in dimethoxyethane (325 ml) and the resulting solution was heated under reflux for 24 hours. Methanol (100 ml) was added to the cooled reaction mixture, and after stirring for an additional 24 hours, the mixture was evaporated to a thick oil. The oil was partitioned between water and ethyl acetate and the organic layer was washed with brine and dried over sodium sulfate. Removal of the solvent and recrystallization of the residue from water gave 1.5 g. Chromatographic purification over silica gel eluting with CHCl3 /MeOH/NH4OH (70:30:3) gave 3-(2-hydroxyethyl)-2,3-dihydro-4,4-dioxo-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazine, mp 158°-160° C.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux for 24 hours
  3. customthe mixture was evaporated to a thick oil
  4. customThe oil was partitioned between water and ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent and recrystallization of the residue from water
  8. customgave 1.5 g
  9. customChromatographic purification over silica gel eluting with CHCl3 /MeOH/NH4OH (70:30:3)

Sources & evidence

ORD record
ord-db83f93778364710ade2433806e4a6f4
Source dataset
uspto-grants-1992_03
Patent number
US05093332

Reaction notes

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