N-methyl-N-trimethylsilylacetamide

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

Procedure: In accordance with the general procedure of Example 1, when 1-chloro-1,2dimethylsilacyclobutane and N-methyl-N-(trimethylsilyl)acetamide are reacted it is predicted that the title compound is obtained.

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

Procedure: To 30.02 g 1-chloro-1-methylsilacyclobutane was added 36.10 g N-methyl-N-(trimethylsilyl)acetamide. The reaction products were fractionally distilled. The title compound was isolated as a clear, colorless fluid with a boiling point of 68°-76° C. at 3.6 mm Hg. The yield was 31.56 g (86%). The product was identified by NMR and mass spectroscopy. The reaction products were fractionally distilled

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

Procedure: Following the general procedure of Example 23, N-methyl-N-trimethylsilylacetamide was reacted with 1-isopropylsulfonyl-2-amino-6-benzoylbenzimidazole in the presence of n-butyl lithium to provide 1-isopropylsulfonyl-2-amino-6-(α-hydroxy-α-methylaminocarbonylmethylbenzyl)benzimidazole. M.P. 92°-95° C.

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

Procedure: Following the general procedure of Example 23, N-methyl-N-trimethylsilylacetamide was reacted with 1-isopropylsulfonyl-2-amino-6-benzoylbenzimidazole in the presence of n-butyl lithium to provide 1-isopropylsulfonyl-2-amino-6-(α-hydroxy-α-methylaminocarbonylmethylbenzyl)benzimidazole. M.P. 92°-95° C.

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

Procedure: In accordance with the general procedure of Example 1, when 1-chloro-1,2-dimethylsilacyclobutane and N-methyl-N-(trimethylsilyl)acetamide are reacted it is predicted that the title compound is obtained.

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

Procedure: In accordance with the general procedure of Example 1, when 1-chloro-1,2-dimethylsilacyclobutane and N-methyl-N-(trimethylsilyl)acetamide are reacted it is predicted that the title compound is obtained.

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

Procedure: To 30.02 g 1-chloro-1-methylsilacyclobutane was added 36.10 g N-methyl-N-(trimethylsilyl)acetamide. The reaction products were fractionally distilled. The title compound was isolated as a clear, colorless fluid with a boiling point of 68°-76° C. at 3.6 mm Hg. The yield was 31.56 g (86%). The product was identified by NMR and mass spectroscopy. The reaction products were fractionally distilled

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

Procedure: Isonipecotic acid (4-piperidinecarboxylic acid) (0.76 g, 6 mmol), N-methyl-N-trimethylsilylacetamide and 3 drops of pyridine were stirred at room temperature for 2 hours. This suspension was added to a filtered solution of 2,2'-dithiobisbenzoyl chloride (1.0 g, 3.0 mmol) in 15 mL of dichloromethane. The solvent was removed after 18 hours and the residue was triturated with 1N HCl. The acid was decanted and the residue was dissolved in acetonitrile. After standing for 24 hours a precipitate formed. The solid was collected and dried to give 0.56 g of the title compound, mp >250° C.; The solvent was removed after 18 hours the residue was triturated with 1N HCl The acid was decanted the residue was dissolved in acetonitrile a precipitate formed The solid was collected dried

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

Procedure: A slurry of (R)-2-amino-2-phenylethanol (1.0 g, 7.4 mmol) in 50 mL dichloromethane was allowed to stir with N-methyl-N-(trimethylsilyl)acetamide (3.4 mL, 21.1 mmol) until a homogenous solution occured. The solution was cooled to 0° C. to 5° C. and a solution of 2,2'-dithiobis[benzoyl chloride] (1.0 g, 2.9 mmol) in 20 mL dichloromethane was added. The solution was stirred for 2 hours and 1 mL of 50% aqueous acetic was added causing the crude product to precipitate from solution. This solid was collected by filtration, washed with 1N HCl, water, and recrystallized from dimethylformamide/water to afford 1.2 g of the title compound, mp 235-236° C. The solution was cooled to 0° C. to 5° C. to precipitate from solution This solid was collected by filtration washed with 1N HCl, water recrystallized from dimethylformamide/water

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

Procedure: A slurry of 4-(aminomethyl)benzenesulfonamide hydrochloride hydrate (6.5 gf 29 mmol) in 100 mL pyridine was allowed to stir with N-methyl-N-(trimethylsilyl)acetamide (13.4 mL, 83.0 mmol) until a homogenous solution occurred. The solution was cooled to 0° C. to 5° C. and a solution of 2,2'-dithiobisbenzoyl chloride (4.0 g, 16.0 mmol) in 20 mL dichloromethane was added dropwise. The resulting solution was allowed to stir for 18 hours and the dichloromethane was removed in vacuo. The crude product was precipitated with the addition of water and the resulting solid was collected by filtration. The crude product was recrystallized from a mixture of dimethylformamide, ethanol, and water to yield 3.3 g of the title compound, mp 267-269° C. The solution was cooled to 0° C. to 5° C. the dichloromethane was removed in vacuo The crude product was precipitated with the addition of water the resulting solid was collected by filtration The crude product was recrystallized from a mixture of dimethylformamide, ethanol, and water

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

Procedure: A slurry of 4-(aminomethyl)benzenesulfonamide hydrochloride hydrate (6.5 gf 29 mmol) in 100 mL pyridine was allowed to stir with N-methyl-N-(trimethylsilyl)acetamide (13.4 mL, 83.0 mmol) until a homogenous solution occurred. The solution was cooled to 0° C. to 5° C. and a solution of 2,2'-dithiobisbenzoyl chloride (4.0 g, 16.0 mmol) in 20 mL dichloromethane was added dropwise. The resulting solution was allowed to stir for 18 hours and the dichloromethane was removed in vacuo. The crude product was precipitated with the addition of water and the resulting solid was collected by filtration. The crude product was recrystallized from a mixture of dimethylformamide, ethanol, and water to yield 3.3 g of the title compound, mp 267-269° C. The solution was cooled to 0° C. to 5° C. the dichloromethane was removed in vacuo The crude product was precipitated with the addition of water the resulting solid was collected by filtration The crude product was recrystallized from a mixture of dimethylformamide, ethanol, and water

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

Procedure: Isonipecotic acid (4-piperidinecarboxylic acid) (0.76 g, 6 mmol), N-methyl-N-trimethylsilylacetamide and 3 drops of pyridine were stirred at room temperature for 2 hours. This suspension was added to a filtered solution of 2,2'-dithiobisbenzoyl chloride (1.0 g, 3.0 mmol) in 15 mL of dichloromethane. The solvent was removed after 18 hours and the residue was triturated with 1N HCl. The acid was decanted and the residue was dissolved in acetonitrile. After standing for 24 hours a precipitate formed. The solid was collected and dried to give 0.56 g of the title compound, mp>250° C.; The solvent was removed after 18 hours the residue was triturated with 1N HCl The acid was decanted the residue was dissolved in acetonitrile a precipitate formed The solid was collected dried