tert-butyl N-(2-amino-5-chlorophenyl)-N-methylcarbamate

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

实验步骤: A mixture of N-(2-nitro-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (6.0 g), dioxane (150 ml), water (30 ml), sodium hydrosulfite (14.6 g) and sodium hydrogencarbonate (17.6 g) was heated under reflux for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate/n-hexane (1/3) as the eluant to afford the title compound (2.98 g). Rf=0.23 (thin-layer chromatography on a silica gel plate using ethyl acetate/n-hexane (1/3) as the eluant). was heated under reflux for 30 minutes The reaction mixture was partitioned between ethyl acetate and water The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate concentrated The residue was chromatographed on a silica gel column

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

实验步骤: To a mixture of N-(2-amino-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (2.50 g) (obtained in Reference Example 2), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (3.01 g) (obtained in Reference Example 6), triethylamine (1.49 ml) and anhydrous tetrahydrofuran (50 ml) was added diethyl cyanophosphonate (1.75 g) and the resulting mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The resulting residue was chromatographed on a silica gel column using n-hexane/ethyl acetate (2/1) as the eluant to give the desired product (3.26 g). Rf=0.41 (thin-layer chromatography on a silica gel plate using n-hexane/ethyl acetate (2/3) as the eluant). The reaction mixture was concentrated the residue partitioned between ethyl acetate and water The ethyl acetate layer was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate evaporated in vacuo The resulting residue was chromatographed on a silica gel column

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

实验步骤: A mixture of N-(2-nitro-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (6.0 g), dioxane (150 ml), water (30 ml), sodium hydrosulfite (14.6 g) and sodium hydrogencarbonate (17.6 g) was heated under reflux for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate/n-hexane (1/3) as the eluant to afford the title compound (2.98 g). Rf=0.23 (thin-layer chromatography on a silica gel plate using ethyl acetate/n-hexane (1/3) as the eluant). was heated under reflux for 30 minutes The reaction mixture was partitioned between ethyl acetate and water The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate concentrated The residue was chromatographed on a silica gel column

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

实验步骤: A mixture of N-(2-nitro-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (6.0 g), dioxane (150 ml), water (30 ml), sodium hydrosulfite (14.6 g) and sodium hydrogencarbonate (17.6 g) was heated under reflux for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate/n-hexane (1/3) as the eluant to afford the title compound (2.98 g). Rf=0.23 (thin-layer chromatography on a silica gel plate using ethyl acetate/n-hexane (1/3) as the eluant). was heated under reflux for 30 minutes The reaction mixture was partitioned between ethyl acetate and water The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate concentrated The residue was chromatographed on a silica gel column

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

实验步骤: To a mixture of N-(2-amino-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (2.50 g) (obtained in Reference Example 2), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (3.01 g) (obtained in Reference Example 6), triethylamine (1.49 ml) and anhydrous tetrahydrofuran (50 ml) was added diethyl cyanophosphonate (1.75 g) and the resulting mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The resulting residue was chromatographed on a silica gel column using n-hexane/ethyl acetate (2/1) as the eluant to give the desired product (3.26 g). Rf=0.41 (thin-layer chromatography on a silica gel plate using n-hexane/ethyl acetate (2/3) as the eluant). The reaction mixture was concentrated the residue partitioned between ethyl acetate and water The ethyl acetate layer was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate evaporated in vacuo The resulting residue was chromatographed on a silica gel column

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

实验步骤: To a mixture of N-(2-amino-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (2.50 g) (obtained in Reference Example 2), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (3.01 g) (obtained in Reference Example 6), triethylamine (1.49 ml) and anhydrous tetrahydrofuran (50 ml) was added diethyl cyanophosphonate (1.75 g) and the resulting mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The resulting residue was chromatographed on a silica gel column using n-hexane/ethyl acetate (2/1) as the eluant to give the desired product (3.26 g). Rf=0.41 (thin-layer chromatography on a silica gel plate using n-hexane/ethyl acetate (2/3) as the eluant). The reaction mixture was concentrated the residue partitioned between ethyl acetate and water The ethyl acetate layer was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate evaporated in vacuo The resulting residue was chromatographed on a silica gel column

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

实验步骤: A mixture of N-(2-nitro-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (6.0 g), dioxane (150 ml), water (30 ml), sodium hydrosulfite (14.6 g) and sodium hydrogencarbonate (17.6 g) was heated under reflux for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water. The extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and then concentrated. The residue was chromatographed on a silica gel column using ethyl acetate/n-hexane (1/3) as the eluant to afford the title compound (2.98 g). Rf=0.23 (thin-layer chromatography on a silica gel plate using ethyl acetate/n-hexane (1/3) as the eluant). was heated under reflux for 30 minutes The reaction mixture was partitioned between ethyl acetate and water The extract was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate concentrated The residue was chromatographed on a silica gel column

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

实验步骤: To a mixture of N-(2-amino-5-chlorophenyl)-N-methylcarbamic acid t-butyl ester (2.50 g) (obtained in Reference Example 2), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (3.01 g) (obtained in Reference Example 6), triethylamine (1.49 ml) and anhydrous tetrahydrofuran (50 ml) was added diethyl cyanophosphonate (1.75 g) and the resulting mixture was stirred at room temperature for 10 hours. The reaction mixture was concentrated and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The resulting residue was chromatographed on a silica gel column using n-hexane/ethyl acetate (2/1) as the eluant to give the desired product (3.26 g). Rf=0.41 (thin-layer chromatography on a silica gel plate using n-hexane/ethyl acetate (2/3) as the eluant). The reaction mixture was concentrated the residue partitioned between ethyl acetate and water The ethyl acetate layer was washed with saturated aqueous sodium chloride solution dried over anhydrous sodium sulfate evaporated in vacuo The resulting residue was chromatographed on a silica gel column