benzyl N-chlorosulfonylcarbamate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedure of Example 7 was followed scaling the reaction to 0.2 moles each of benzyl alcohol and chlorosulfonyl isocyanate to give benzyloxycarbonylsulfamoyl chloride.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 43.5 ml (0.5 mole) of chlorosulfonyl isocyanate in 400 ml of methylene chloride, stirred in an ice bath, was added 51.6 ml (0.5 mole) of benzyl alcohol over an one hr period. The reaction mixture was concentrated under reduced pressure and the solid residue was triturated in petroleum ether (bp range 35°-65° C.). The solid was collected by filtration, rinsed twice with petroleum ether and dried under vacuum to give 110 g (88% yield) of benzyloxycarbonylsulfamoyl chloride. The reaction mixture was concentrated under reduced pressure the solid residue was triturated in petroleum ether (bp range 35°-65° C.) The solid was collected by filtration rinsed twice with petroleum ether dried under vacuum

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: Isopropyl acetate (300 mL) was charged into a 1000 ml 3-neck flask and cooled to −10˜−5° C. Sulfurisocyanatidic chloride (44.5 mL) was added at −5˜10° C. followed by the addition of phenylmethanol (50.5 mL) in isopropyl acetate (60 mL) at −5˜10° C. over 60 minutes. The mixture reacted at −5˜10° C. and was monitored by HPLC until the content of benzyl alcohol was <2% (after 1 hour at 0° C.). A mixture of acetonitrile (300 mL), 3-methylazetidine hydrochloride (50 g) (Intermediate C, either commercially available or prepared as set out below) and triethylamine (162 mL) was stirred in a 2000 mL 3-neck flask and to this was added the solution of the intermediate benzyl chlorosulfonylcarbamate in isopropyl acetate (360 mL) dropwise at <−5° C. over 90 minutes. The mixture was allowed to warm to RT overnight. The reaction was quenched with acetic acid and pH was adjusted to 4-5. The mixture was separated and the aqueous phase was washed with isopropyl acetate (500 ml) and then separated. The organic phase was combined and washed with 10% brine (2×120 ml), dried with anhydrous magnesium sulphate, filtered and the filter cake washed with isopropyl acetate (30 ml) and filtered to afford the sub-title product (145 g) as a red oil. cooled to −10˜−5° C The mixture reacted at −5˜10° C. <2% (after 1 hour at 0° C.) commercially available or prepared The reaction was quenched with acetic acid and pH The mixture was separated the aqueous phase was washed with isopropyl acetate (500 ml) separated washed with 10% brine (2×120 ml) dried with anhydrous magnesium sulphate filtered the filter cake washed with isopropyl acetate (30 ml) filtered

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedure of Example 7 was followed scaling the reaction to 0.2 moles each of benzyl alcohol and chlorosulfonyl isocyanate to give benzyloxycarbonylsulfamoyl chloride.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: The procedure of Example 7 was followed scaling the reaction to 0.2 moles each of benzyl alcohol and chlorosulfonyl isocyanate to give benzyloxycarbonylsulfamoyl chloride.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 43.5 ml (0.5 mole) of chlorosulfonyl isocyanate in 400 ml of methylene chloride, stirred in an ice bath, was added 51.6 ml (0.5 mole) of benzyl alcohol over an one hr period. The reaction mixture was concentrated under reduced pressure and the solid residue was triturated in petroleum ether (bp range 35°-65° C.). The solid was collected by filtration, rinsed twice with petroleum ether and dried under vacuum to give 110 g (88% yield) of benzyloxycarbonylsulfamoyl chloride. The reaction mixture was concentrated under reduced pressure the solid residue was triturated in petroleum ether (bp range 35°-65° C.) The solid was collected by filtration rinsed twice with petroleum ether dried under vacuum

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 43.5 ml (0.5 mole) of chlorosulfonyl isocyanate in 400 ml of methylene chloride, stirred in an ice bath, was added 51.6 ml (0.5 mole) of benzyl alcohol over an one hr period. The reaction mixture was concentrated under reduced pressure and the solid residue was triturated in petroleum ether (bp range 35°-65° C.). The solid was collected by filtration, rinsed twice with petroleum ether and dried under vacuum to give 110 g (88% yield) of benzyloxycarbonylsulfamoyl chloride. The reaction mixture was concentrated under reduced pressure the solid residue was triturated in petroleum ether (bp range 35°-65° C.) The solid was collected by filtration rinsed twice with petroleum ether dried under vacuum

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir: