cyclopentanesulfonamide

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

Procedure: 2-(2,2-Dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-(4-fluoro-benzyl)-N-methoxy-acetamide was treated with cyclopentanesulfonic acid amide as described in the preparation of compound 1 to yield the title compound. 1H NMR (500 MHz, CDCl3) δ: 1.66 (m, 2), 1.83 (m, 2), 2.08 (overlapping m, 4), 3.69 (s, 3), 4.10 (p, 1, J=8), 4.79 (s, 2), 6.53 (s, 1), 7.01 (m, 2), 7.29 (m, 2), 8.84 (s, 1). 13C NMR (125 MHz, CDCl3) δ: 20.55, 22.24, 42.90, 57.27, 57.80, 87.06, 110.29, 110.46, 124.85, 124.91, 125.66, 153.94, 154.50, 156.29, 158.25, 165.53.

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

Procedure: The general method of procedure A was followed with cyclopentanesulfonamide (3 g), acetone (200 ml), 1N sodium hydroxide (20 ml), and 3,4-dichlorophenyl isocyanate (3.6 g) dissolved in acetone (50 ml). After two hours, 1N HCl (20 ml) was added and the resulting solid diluted with water and collected. After drying at 65° C., 5.5 g of solid product were obtained. collected After drying at 65° C.

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

Procedure: The general method of procedure A was followed with cyclopentanesulfonamide (3 g), acetone (100 ml), 1N sodium hydroxide (21 ml), and 4-bromophenyl isocyanate (3.7 g) dissolved in acetone (50 ml). After two hours, 1N HCl (21 ml) was added. The resulting precipitate was collected, washed with water and dried at 60° C. under vacuum to provide 5.4 g of product. The resulting precipitate was collected washed with water dried at 60° C. under vacuum

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

Procedure: Cyclopentanesulfonamide (9.7 g) was dissolved in acetone (300 ml) and 1N NaOH (65 ml) was added. To the resulting solution was added p-chlorophenylisocyanate (9.5 g) dissolved in acetone (100 ml). The solution was allowed to stir for two hours and was then treated with 1N HCl (65 ml). The resulting solid was collected and treated with 1N NaOH (100 ml). This mixture was treated with 1N HCl (100 ml) and the resulting solid collected. The solid was dissolved in acetone, water was added and the acetone was stripped off. The solid material was collected and dried to provide 12.8 g of product. The resulting solid was collected treated with 1N NaOH (100 ml) This mixture was treated with 1N HCl (100 ml) the resulting solid collected The solid was dissolved in acetone water was added The solid material was collected dried

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

Procedure: The general method of procedure B was followed with cyclopentanesulfonamide (7.45 g), sodium methoxide (2.7 g), methanol (200 ml), tetrahydrofuran (200 ml), and 4-fluorophenyl isocyanate (6.85 g). The residue was dissolved in water and the solution acidified with 1N HCl. The resulting solid was separated and recrystallized from benzene to give 2.9 g of white solid with a melting point of 155-157° C. The resulting solid was separated recrystallized from benzene

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

Procedure: The general method of procedure A was followed with cyclopentanesulfonamide (3 g), acetone (200 ml), 1N sodium hydroxide (20 ml), and 3,4-dichlorophenyl isocyanate (3.6 g) dissolved in acetone (50 ml). After two hours, 1N HCl (20 ml) was added and the resulting solid diluted with water and collected. After drying at 5° C., 5.5 g of solid product were obtained. collected After drying at 5° C.

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

Procedure: Cyclopentanesulfonamide (9.7 g) was dissolved in acetone (300 ml) and 1N NaOH (65 ml) was added. To the resulting solution was added p-chlorophenylisocyanate (9.5 g) dissolved in acetone (100 ml). The solution was allowed to stir for two hours and was then treated with 1N HCl (65 ml). The resulting solid was collected and treated with 1N NaOH (100 ml). This mixture was treated with 1N HCl (100 ml) and the resulting solid collected. The solid was dissolved in acetone, water was added and the acetone was stripped off. The solid material was collected and dried to provide 12.8 g of product. The resulting solid was collected treated with 1N NaOH (100 ml) This mixture was treated with 1N HCl (100 ml) the resulting solid collected The solid was dissolved in acetone water was added The solid material was collected dried

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

Procedure: The general method of procedure B was followed with cyclopentanesulfonamide (7.45 g), sodium methoxide (2.7 g), methanol (200 ml), tetrahydrofuran (200 ml), and 4-fluorophenyl isocyanate (6.85 g). The residue was dissolved in water and the solution acidified with 1N HCl. The resulting solid was separated and recrystallized from benzene to give 2.9 g of white solid with a melting point of 155°-157° C. The resulting solid was separated recrystallized from benzene

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

Procedure: According to Reference Example 9-7, by use of cyclopentanesulfonyl chloride (300 mg, 1.8 mmol) and a 7 mol/L solution of ammonia in methanol (2 mL), the mixture was stirred and reacted at room temperature for 4 hours. After slurry purification using chloroform, purification by silica gel column chromatography (chloroform/methanol=1/0 to 20/1) was performed to give cyclopentanesulfonamide (Compound FP) (173 mg, yield: 66%). reacted at room temperature for 4 hours purification chloroform, purification by silica gel column chromatography (chloroform/methanol=1/0 to 20/1)