benzyl N-(2-sulfamoylethyl)carbamate

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

Procedure: Crude 2-(N-benzyloxycarbonylamino)ethanesulfonyl chloride was dissolved in acetonitrile (10 mL). The resulting solution was cooled on an ice/water bath and a solution 1:1 of 28% NH4OH (5 mL) and acetonitrile (5 mL) was dropped therein. After stirring for 30′, the solvents were evaporated off under vacuum and the crude residue was recrystallised with methanol to give 2-(N-benzyloxycarbonylamino)ethanesulfonamide as white powder (0.51 g; 1.96 mmol). The resulting solution was cooled on an ice/water bath were evaporated off under vacuum the crude residue was recrystallised with methanol

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

Procedure: Take a suspension of 100 g of Cbz-Taurinamide in 1000 ml methanol, and 10% Pd/C (1.0 g) and subject to hydrogenation at 45-50 psi. Upon completion of the reaction filter the catalyst and add succinic acid (1.0 eq) to the solvent and distill off the solvent under vacuum to provide the title compound in about 90% yield as a white solid. Upon completion of the reaction filter the catalyst distill off the solvent under vacuum

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

Procedure: Crude 2-(N-benzyloxycarbonylamino)ethanesulfonyl chloride was dissolved in acetonitrile (10 mL). The resulting solution was cooled on an ice/water bath and a solution 1:1 of 28% NH4OH (5 mL) and acetonitrile (5 mL) was dropped therein. After stirring for 30′, the solvents were evaporated off under vacuum and the crude residue was recrystallised with methanol to give 2-(N-benzyloxycarbonylamino)ethanesulfonamide as white powder (0.51 g; 1.96 mmol). The resulting solution was cooled on an ice/water bath were evaporated off under vacuum the crude residue was recrystallised with methanol

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

Procedure: In a reaction flask, 10.3 g of 2-benzyloxyformamidoethylsulfonamide, 10% Pd/C (3.0 g) and 600 ml of methanol were added. The mixture was stirred at room temperature overnight under hydrogen atmosphere, added with 35 ml of formic acid, stirred for 30 min, filtered, and concentrated under a reduced pressure to obtain 5.6 g of oily product, yield 93%. stirred for 30 min filtered concentrated under a reduced pressure

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

Procedure: In a reaction flask, 100 ml of aqueous ammonia and 100 ml of dioxane were added, and a solution of 17.9 g 2-benzyloxyformamidoethylsulfonyl chloride in acetonitrile (30 ml) was added dropwise under ice-bath condition. The mixture was stirred for 2 h at room temperature. Upon the end of the dropping, the mixture was concentrated under a reduced pressure, and was then filtered, the filter cake was washed with water, and dried to obtain 12.3 g of white solid, yield 74%. Upon the end of the dropping, the mixture was concentrated under a reduced pressure was then filtered the filter cake was washed with water dried