Methoxycarbonylsulfamoyl Chloride

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Triethylamine (3.46 mL) in DCM (5 mL) was stirred under nitrogen and to the solution was added a solution of methyl chlorosulfonylcarbamate (1.658 g) in DCM (5 mL). The mixture was stirred at room temperature for 15 min then a solution of (S)-tert-butyl 2-((S)-1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate (1.74 g) in DCM (5 mL) was added. Stirring was continued overnight. The reaction mixture was washed with water then brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude product was purified by flash silica chromatography eluting with 40% ethyl acetate in isohexane to give the title compound (1.2 g) as a white solid. Stirring was continued overnight The reaction mixture was washed with water brine, dried over magnesium sulfate filtered concentrated in vacuo Crude product was purified by flash silica chromatography eluting with 40% ethyl acetate in isohexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Triethylamine (3.46 mL) in DCM (5 mL) was stirred under nitrogen and to the solution was added a solution of methyl chlorosulfonylcarbamate (1.658 g) in DCM (5 mL). The mixture was stirred at room temperature for 15 min then a solution of (S)-tert-butyl 2-((S)-1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate (1.74 g) in DCM (5 mL) was added. Stirring was continued overnight. The reaction mixture was washed with water then brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude product was purified by flash silica chromatography eluting with 40% ethyl acetate in isohexane to give the title compound (1.2 g) as a white solid. Stirring was continued overnight The reaction mixture was washed with water brine, dried over magnesium sulfate filtered concentrated in vacuo Crude product was purified by flash silica chromatography eluting with 40% ethyl acetate in isohexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of methanol (10.2 mL, 252 mmoles) in 15 mL toluene was added dropwise to a solution of chlorosulfonyl isocyanate (22.0 mL, 252 mmoles) in 75 mL toluene at 0° C. The mixture was removed from the cooling bath and stirred for one-half hour at room temperature, then cooled to 0° C. and 65 mL ice cold hexanes was added. The white precipitate was collected by filtration and washed two times with a small amount of cold hexanes and dried in vacuo to give 33.0 g of a white solid, mp 72°-74° C. The mixture was removed from the cooling bath cooled to 0° C. 65 mL ice cold hexanes was added The white precipitate was collected by filtration washed two times with a small amount of cold hexanes dried in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of methanol (10.2 mL, 252 mmoles) in 15 mL toluene was added dropwise to a solution of chlorosulfonyl isocyanate (22.0 mL, 252 mmoles) in 75 mL toluene at 0° C. The mixture was removed from the cooling bath and stirred for one-half hour at room temperature, then cooled to 0° C. and 65 mL ice cold hexanes was added. The white precipitate was collected by filtration and washed two times with a small amount of cold hexanes and dried in vacuo to give 33.0 g of a white solid, mp 72°-74° C. The mixture was removed from the cooling bath cooled to 0° C. 65 mL ice cold hexanes was added The white precipitate was collected by filtration washed two times with a small amount of cold hexanes dried in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of methanol (10.2 mL, 252 mmoles) in 15 mL toluene was added dropwise to a solution of chlorosulfonyl isocyanate (22.0 mL, 252 mmoles) in 75 mL toluene at 0° C. The mixture was removed from the cooling bath and stirred for one-half hour at room temperature, then cooled to 0° C. and 65 mL ice cold hexanes was added. The white precipitate was collected by filtration and washed two times with a small amount of cold hexanes and dried in vacuo to give 33.0 g of a white solid, mp 72°-74° C. The mixture was removed from the cooling bath cooled to 0° C. 65 mL ice cold hexanes was added The white precipitate was collected by filtration washed two times with a small amount of cold hexanes dried in vacuo

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of methanol (10.2 mL, 252 mmoles) in 15 mL toluene was added dropwise to a solution of chlorosulfonyl isocyanate (22.0 mL, 252 mmoles) in 75 mL toluene at 0° C. The cooling bath was removed and stirred for one-half hour at room temperature. This was then cooled to 0° C. and 65 mL ice cold hexanes was added. The white precipitate was collected by filtration and washed 2 times with a small amount of cold hexane to give 33.0 g of a white solid, mp 72°-74° C. The cooling bath was removed This was then cooled to 0° C. 65 mL ice cold hexanes was added The white precipitate was collected by filtration washed 2 times with a small amount of cold hexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of methanol (10.2 mL, 252 mmoles) in 15 mL toluene was added dropwise to a solution of chlorosulfonyl isocyanate (22.0 mL, 252 mmoles) in 75 mL toluene at 0° C. The cooling bath was removed and stirred for one-half hour at room temperature. This was then cooled to 0° C. and 65 mL ice cold hexanes was added. The white precipitate was collected by filtration and washed 2 times with a small amount of cold hexane to give 33.0 g of a white solid, mp 72°-74° C. The cooling bath was removed This was then cooled to 0° C. 65 mL ice cold hexanes was added The white precipitate was collected by filtration washed 2 times with a small amount of cold hexane

反应条件: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl chlorosulfonylcarbamate (27.90 g, 0.16 mol) was dissolved in CH2Cl2 (100 mL) and cooled to −20° C. To the solution of methyl chlorosulfonylcarbamate, was dropwisely added 2,6-dichloro-4-(trifluoromethyl)aniline (2.50 g, 10.7 mmol) and triethylamine (2.53 g, 32.1 mmol) in CH2Cl2 (70 mL) and agitated for 12 hr at room temperature. The reaction mixture was added with water (100 mL) for extraction to obtain the organic layer. The resultant was dried over MgSO4, concentrated under reduced pressure, and purified by column chromatography (hexane:ethyl acetate=7:3), giving the compound of interest (2.11 g, 6%, yellow solid). 1H NMR (300 MHz, CDCl3): δ 7.57 (s, 2H), 3.84 (s, 3H). to obtain the organic layer The resultant was dried over MgSO4 concentrated under reduced pressure purified by column chromatography (hexane:ethyl acetate=7:3) giving the compound of interest (2.11 g, 6%, yellow solid)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Triethylamine (3.46 mL) in DCM (5 mL) was stirred under nitrogen and to the solution was added a solution of methyl chlorosulfonylcarbamate (1.658 g) in DCM (5 mL). The mixture was stirred at room temperature for 15 min then a solution of (S)-tert-butyl 2-((S)-1-amino-3-(6-bromopyridin-3-yl)-1-oxopropan-2-ylcarbamoyl)piperidine-1-carboxylate (1.74 g) in DCM (5 mL) was added. Stirring was continued overnight. The reaction mixture was washed with water then brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Crude product was purified by flash silica chromatography eluting with 40% ethyl acetate in isohexane to give the title compound (1.2 g) as a white solid. Stirring was continued overnight The reaction mixture was washed with water brine, dried over magnesium sulfate filtered concentrated in vacuo Crude product was purified by flash silica chromatography eluting with 40% ethyl acetate in isohexane

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of methanol (10.2 mL, 252 mmoles) in 15 mL toluene was added dropwise to a solution of chlorosulfonyl isocyanate (22.0 mL, 252 mmoles) in 75 mL toluene at 0° C. The mixture was removed from the cooling bath and stirred for one-half hour at room temperature, then cooled to 0° C. and 65 mL ice cold hexanes was added. The white precipitate was collected by filtration and washed two times with a small amount of cold hexanes and dried in vacuo to give 33.0 g of a white solid, mp 72°-74° C. The mixture was removed from the cooling bath cooled to 0° C. 65 mL ice cold hexanes was added The white precipitate was collected by filtration washed two times with a small amount of cold hexanes dried in vacuo