2-methoxy-N-[2-(2-methoxyethoxy)ethyl]ethanamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 g, 9 mmol) in dry DMF (25 ml) was added hydroxybenzotriazole hydrate (1.22 g, 9 mmol), N-methoxyethoxyethyl-N-methoxyethylamine (3.19 g, 18 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.59 g, 14 mmol), and the resulting reaction mixture was stirred overnight. Water (10 ml) was added, the mixture stirred an additional 2 hours and concentrated to dryness under reduced pressure. The residue was treated with 0.5N HCl and the pH adjusted to 6.5-6.9 by the additon of dilute NH4OH. The aqueous mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried over sodium sulfate. After filtration and removal of the solvent, the residue was recrystallized from water to give N-methoxyethoxyethyl-N-methoxyethyl-(2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno-[2,3-b][1,4]thiazin-3-yl)acetamide, mp 156°-158° C. the resulting reaction mixture the mixture stirred an additional 2 hours concentrated to dryness under reduced pressure The residue was treated with 0.5N HCl The aqueous mixture was extracted with ethyl acetate the combined extracts were washed with brine dried over sodium sulfate After filtration and removal of the solvent the residue was recrystallized from water

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 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 g, 9 mmol) in dry DMF (25 ml) was added hydroxybenzotriazole hydrate (1.22 g, 9 mmol), N-methoxyethoxyethyl-N-methoxyethylamine (3.19 g, 18 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.59 g, 14 mmol), and the resulting reaction mixture was stirred overnight. Water (10 ml) was added, the mixture stirred an additional 2 hours and concentrated to dryness under reduced pressure. The residue was treated with 0.5N HCl and the pH adjusted to 6.5-6.9 by the additon of dilute NH4OH. The aqueous mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried over sodium sulfate. After filtration and removal of the solvent, the residue was recrystallized from water to give N-methoxyethoxyethyl-N-methoxyethyl-(2,3-dihydro-2,4,4-trioxo-6-sulfamoyl-1H-thieno-[2,3-b][1,4]thiazin-3-yl)acetamide, mp 156°-158° C. the resulting reaction mixture the mixture stirred an additional 2 hours concentrated to dryness under reduced pressure The residue was treated with 0.5N HCl The aqueous mixture was extracted with ethyl acetate the combined extracts were washed with brine dried over sodium sulfate After filtration and removal of the solvent the residue was recrystallized from water