methyl 2-(benzenesulfonamido)acetate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 47.5 g (0.6 mol) sample of pyridine was added dropwise to a stirred and cooled (ice bath) slurry of 53.0 g (0.3 mol) benzenesulfonyl chloride and 37.7 g (0.3 mol) glycine methyl ester hydrochloride in 500 ml dichloromethane. The reaction mixture was then allowed to warm to 25° C. and was stirred for about 16 hours. The reaction mixture was diluted with 250 ml water, the organic layer was separated, washed with water, washed with 10% aqueous hydrochloric acid solution, washed with water, dried over magnesium sulfate and evaporated to give 36.5 g N-(methoxycarbonylmethyl)benzenesulfonamide, which crystallized as a colorless solid melting at 62°-63° C. A 3.5 g (0.035 mol) sample of triethylamine was added dropwise to a solution of 8 g (0.035 mol) N-methoxycarbonylmethyl)benzenesulfonamide and 6.5 g (0.035 mol) trichloromethylsulfenyl chloride in 150 ml dichloromethane. The reaction mixture was then stirred at about 25° C. for about 1 hour, washed with water, dried over magnesium sulfate and evaporated to give 7.5 g of N-methoxycarbonylmethyl-N-trichloromethylthiobenzenesulfonamide, which crystallized as a colorless solid melting at 61°-62° C. The compound is tabulated in Table I as Compound No. 1. was stirred for about 16 hours the organic layer was separated washed with water washed with 10% aqueous hydrochloric acid solution washed with water dried over magnesium sulfate evaporated

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 47.5 g (0.6 mol) sample of pyridine was added dropwise to a stirred and cooled (ice bath) slurry of 53.0 g (0.3 mol) benzenesulfonyl chloride and 37.7 g (0.3 mol) glycine methyl ester hydrochloride in 500 ml dichloromethane. The reaction mixture was then allowed to warm to 25° C. and was stirred for about 16 hours. The reaction mixture was diluted with 250 ml water, the organic layer was separated, washed with water, washed with 10% aqueous hydrochloric acid solution, washed with water, dried over magnesium sulfate and evaporated to give 36.5 g N-(methoxycarbonylmethyl)benzenesulfonamide, which crystallized as a colorless solid melting at 62°-63° C. A 3.5 g (0.035 mol) sample of triethylamine was added dropwise to a solution of 8 g (0.035 mol) N-methoxycarbonylmethyl)benzenesulfonamide and 6.5 g (0.035 mol) trichloromethylsulfenyl chloride in 150 ml dichloromethane. The reaction mixture was then stirred at about 25° C. for about 1 hour, washed with water, dried over magnesium sulfate and evaporated to give 7.5 g of N-methoxycarbonylmethyl-N-trichloromethylthiobenzenesulfonamide, which crystallized as a colorless solid melting at 61°-62° C. The compound is tabulated in Table I as Compound No. 1. was stirred for about 16 hours the organic layer was separated washed with water washed with 10% aqueous hydrochloric acid solution washed with water dried over magnesium sulfate evaporated

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 47.5 g (0.6 mol) sample of pyridine was added dropwise to a stirred and cooled (ice bath) slurry of 53.0 g (0.3 mol) benzenesulfonyl chloride and 37.7 g (0.3 mol) glycine methyl ester hydrochloride in 500 ml dichloromethane. The reaction mixture was then allowed to warm to 25° C. and was stirred for about 16 hours. The reaction mixture was diluted with 250 ml water, the organic layer was separated, washed with water, washed with 10% aqueous hydrochloric acid solution, washed with water, dried over magnesium sulfate and evaporated to give 36.5 g N-(methoxycarbonylmethyl)benzenesulfonamide, which crystallized as a colorless solid melting at 62°-63° C. was stirred for about 16 hours the organic layer was separated washed with water washed with 10% aqueous hydrochloric acid solution washed with water dried over magnesium sulfate evaporated

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 47.5 g (0.6 mol) sample of pyridine was added dropwise to a stirred and cooled (ice bath) slurry of 53.0 g (0.3 mol) benzenesulfonyl chloride and 37.7 g (0.3 mol) glycine methyl ester hydrochloride in 500 ml dichloromethane. The reaction mixture was then allowed to warm to 25° C. and was stirred for about 16 hours. The reaction mixture was diluted with 250 ml water, the organic layer was separated, washed with water, washed with 10% aqueous hydrochloric acid solution, washed with water, dried over magnesium sulfate and evaporated to give 36.5 g N-(methoxycarbonylmethyl)benzenesulfonamide, which crystallized as a colorless solid melting at 62°-63° C. was stirred for about 16 hours the organic layer was separated washed with water washed with 10% aqueous hydrochloric acid solution washed with water dried over magnesium sulfate evaporated

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

実験手順: According to the conditions reported by Anthony et al (WO 02/30931 A2) for the preparation of 3-[(benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]pyridine-2-carboxylic acid isopropyl ester, a solution of diisopropyl azodicarboxylate (1.07 g, 5.30 mmol) in THF (5 mL) was added dropwise over 40 min to a stirred solution of 3-hydroxymethyl-6-methyl-pyridine-2-carboxylic acid isopropyl ester (739 mg, 3.53 mmol), N-(phenylsulphonyl)glycine methyl ester (810 mg, 3.53 mmol) and triphenylphosphine (1.39 g, 5.30 mol) in THF (15 mL) The resulting solution was then left to stir at room temperature overnight. The reaction mixture was concentrated to give crude 3-[(benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]-6-methylpyridine-2-carboxylic acid isopropyl ester as a golden syrup. This was used in the subsequent step without further purification.—Selected 1H NMR (CDCl3): δ 4.73 (s, 2H), 4.00 (s, 2H), 3.54 (s, 3H), 2.70 (s, 3H). was then left The reaction mixture was concentrated

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

実験手順: According to the conditions reported by Anthony et al (WO 02/30931 A2) for the preparation of 3-[(benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]pyridine-2-carboxylic acid isopropyl ester, a solution of diisopropyl azodicarboxylate (1.07 g, 5.30 mmol) in THF (5 mL) was added dropwise over 40 min to a stirred solution of 3-hydroxymethyl-6-methyl-pyridine-2-carboxylic acid isopropyl ester (739 mg, 3.53 mmol), N-(phenylsulphonyl)glycine methyl ester (810 mg, 3.53 mmol) and triphenylphosphine (1.39 g, 5.30 mol) in THF (15 mL) The resulting solution was then left to stir at room temperature overnight. The reaction mixture was concentrated to give crude 3-[(benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]-6-methylpyridine-2-carboxylic acid isopropyl ester as a golden syrup. This was used in the subsequent step without further purification.—Selected 1H NMR (CDCl3): δ 4.73 (s, 2H), 4.00 (s, 2H), 3.54 (s, 3H), 2.70 (s, 3H). was then left The reaction mixture was concentrated

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 47.5 g (0.6 mol) sample of pyridine was added dropwise to a stirred and cooled (ice bath) slurry of 53.0 g (0.3 mol) benzenesulfonyl chloride and 37.7 g (0.3 mol) glycine methyl ester hydrochloride in 500 ml dichloromethane. The reaction mixture was then allowed to warm to 25° C. and was stirred for about 16 hours. The reaction mixture was diluted with 250 ml water, the organic layer was separated, washed with water, washed with 10% aqueous hydrochloric acid solution, washed with water, dried over magnesium sulfate and evaporated to give 36.5 g N-(methoxycarbonylmethyl)benzenesulfonamide, which crystallized as a colorless solid melting at 62°-63° C. was stirred for about 16 hours the organic layer was separated washed with water washed with 10% aqueous hydrochloric acid solution washed with water dried over magnesium sulfate evaporated

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 47.5 g (0.6 mol) sample of pyridine was added dropwise to a stirred and cooled (ice bath) slurry of 53.0 g (0.3 mol) benzenesulfonyl chloride and 37.7 g (0.3 mol) glycine methyl ester hydrochloride in 500 ml dichloromethane. The reaction mixture was then allowed to warm to 25° C. and was stirred for about 16 hours. The reaction mixture was diluted with 250 ml water, the organic layer was separated, washed with water, washed with 10% aqueous hydrochloric acid solution, washed with water, dried over magnesium sulfate and evaporated to give 36.5 g N-(methoxycarbonylmethyl)benzenesulfonamide, which crystallized as a colorless solid melting at 62°-63° C. A 3.5 g (0.035 mol) sample of triethylamine was added dropwise to a solution of 8 g (0.035 mol) N-methoxycarbonylmethyl)benzenesulfonamide and 6.5 g (0.035 mol) trichloromethylsulfenyl chloride in 150 ml dichloromethane. The reaction mixture was then stirred at about 25° C. for about 1 hour, washed with water, dried over magnesium sulfate and evaporated to give 7.5 g of N-methoxycarbonylmethyl-N-trichloromethylthiobenzenesulfonamide, which crystallized as a colorless solid melting at 61°-62° C. The compound is tabulated in Table I as Compound No. 1. was stirred for about 16 hours the organic layer was separated washed with water washed with 10% aqueous hydrochloric acid solution washed with water dried over magnesium sulfate evaporated

反応条件: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A 47.5 g (0.6 mol) sample of pyridine was added dropwise to a stirred and cooled (ice bath) slurry of 53.0 g (0.3 mol) benzenesulfonyl chloride and 37.7 g (0.3 mol) glycine methyl ester hydrochloride in 500 ml dichloromethane. The reaction mixture was then allowed to warm to 25° C. and was stirred for about 16 hours. The reaction mixture was diluted with 250 ml water, the organic layer was separated, washed with water, washed with 10% aqueous hydrochloric acid solution, washed with water, dried over magnesium sulfate and evaporated to give 36.5 g N-(methoxycarbonylmethyl)benzenesulfonamide, which crystallized as a colorless solid melting at 62°-63° C. was stirred for about 16 hours the organic layer was separated washed with water washed with 10% aqueous hydrochloric acid solution washed with water dried over magnesium sulfate evaporated

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

実験手順: According to the conditions reported by Anthony et al (WO 02/30931 A2) for the preparation of 3-[(benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]pyridine-2-carboxylic acid isopropyl ester, a solution of diisopropyl azodicarboxylate (1.07 g, 5.30 mmol) in THF (5 mL) was added dropwise over 40 min to a stirred solution of 3-hydroxymethyl-6-methyl-pyridine-2-carboxylic acid isopropyl ester (739 mg, 3.53 mmol), N-(phenylsulphonyl)glycine methyl ester (810 mg, 3.53 mmol) and triphenylphosphine (1.39 g, 5.30 mol) in THF (15 mL) The resulting solution was then left to stir at room temperature overnight. The reaction mixture was concentrated to give crude 3-[(benzenesulfonyl(methoxycarbonylmethyl)amino)methyl]-6-methylpyridine-2-carboxylic acid isopropyl ester as a golden syrup. This was used in the subsequent step without further purification.—Selected 1H NMR (CDCl3): δ 4.73 (s, 2H), 4.00 (s, 2H), 3.54 (s, 3H), 2.70 (s, 3H). was then left The reaction mixture was concentrated