Methanol → HCID 10333887, compound

HRID 2371418Notes

Reaction equation

HRID 2371418 reaction equation
B.C1COCC1.O=[C:8]1[CH:13]([CH2:14][C:15](O)=[O:16])[S:12][C:11]2[S:18][C:19]([S:21](=[O:24])(=[O:23])[NH2:22])=[CH:20][C:10]=2[NH:9]1.CO>C1COCC1>[OH:16][CH2:15][CH2:14][CH:13]1[S:12][C:11]2[S:18][C:19]([S:21](=[O:23])(=[O:24])[NH2:22])=[CH:20][C:10]=2[NH:9][CH2:8]1

Participants

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 10040931HCID 10040931, compound

Product 1

HCID 10333887HCID 10333887, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of borane/THF (200 ml, 1M, 200 mmol) was added gradually to a solution of (2,3-dihydro-2-oxo-6-sulfamoyl-1H-thieno-[2,3-b]-[1,4]thiazin-3-yl)acetic acid (12.3 g, 40 mmol) in THF (200 ml). The mixture was stirred at ambient temperature until gas evolution ceased and the resulting clear solution was heated under reflux overnight. The reaction mixture was cooled to 25° C. and treated with methanol (200 ml). When gas evolution ceased, the mixture was evaporated to dryness under vacuum and the residue was restripped from methanol two additional times (2×50 ml). Recrystallization of the residue from water gave 6.4 g 3-(2-hydroxyethyl)-2,3-dihydro-6-sulfamoyl-1H-thieno[2,3-b][1,4]thiazine, mp 145°-147° C. An additional 1.2 g of product was isolated from the filtrate on standing. Further recrystallization from water gave material of mp 149°-150° C.

Workup

  1. temperaturethe resulting clear solution was heated
  2. temperatureunder reflux overnight
  3. temperatureThe reaction mixture was cooled to 25° C.
  4. customthe mixture was evaporated to dryness under vacuum
  5. customRecrystallization of the residue from water

Sources & evidence

ORD record
ord-9fd39119afb04f3580cbacba98aa1b63
Source dataset
uspto-grants-1992_03
Patent number
US05093332

Reaction notes

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