1,3-diethoxypropan-2-ol

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

実験手順: The same operation as in Example 1-1 or 1-2 was carried out using trans-2-decenoic acid and 1,3-diethoxy-2-propanol as starting materials to give the aimed compound.

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

実験手順: The same operation as in Example 1-1 or 1-2 was carried out using trans-2-decenoic acid and 1,3-diethoxy-2-propanol as starting materials to give the aimed compound.

反応条件: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: p-Toluenesulfonic acid monohydrate (57 mg) and isobutyl aldehyde (0.41 ml) were added to a solution of ethyl 5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (1.14 g), prepared in step (32a), in methylene chloride solution (17 ml) at −20° C. The mixture was stirred at that temperature for one hr. 1,1′-Carbonyldiimidazole (732 mg) was added to the reaction solution. Further, one hr after that, 1,3-diethoxy-2-propanol (4.70 ml) was added thereto. The reaction solution was cooled to −30° C. Trifluoroacetic acid (0.70 ml) was added thereto. The temperature was raised to room temperature, followed by stirring for 25 hr. 0.5 M hydrochloric acid was added to the reaction solution under ice cooling to stop the reaction, and separation was then carried out. The organic layer was washed five times with a 7% aqueous sodium hydrogencarbonate solution. The solvent was evaporated under reduced pressure. Diethyl ether and water were added to the residue. The organic layer after the separation was successively washed twice with water, with 0.5 M hydrochloric acid, twice with water, and then with 20% saline. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane) to give a crude product of ethyl 2-(1-(1,3-diethoxy-2-propoxycarbonyloxy)-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (1.15 g). The temperature was raised to room temperature by stirring for 25 hr the reaction, and separation The organic layer was washed five times with a 7% aqueous sodium hydrogencarbonate solution The solvent was evaporated under reduced pressure Diethyl ether and water were added to the residue The organic layer after the separation was successively washed twice with water, with 0.5 M hydrochloric acid, twice with water The solvent was evaporated under reduced pressure The residue was purified by column chromatography on silica gel (ethyl acetate/hexane)

反応条件: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: p-Toluenesulfonic acid monohydrate (57 mg) and isobutyl aldehyde (0.41 ml) were added to a solution of ethyl 5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (1.14 g), prepared in step (32a), in methylene chloride solution (17 ml) at −20° C. The mixture was stirred at that temperature for one hr. 1,1′-Carbonyldiimidazole (732 mg) was added to the reaction solution. Further, one hr after that, 1,3-diethoxy-2-propanol (4.70 ml) was added thereto. The reaction solution was cooled to −30° C. Trifluoroacetic acid (0.70 ml) was added thereto. The temperature was raised to room temperature, followed by stirring for 25 hr. 0.5 M hydrochloric acid was added to the reaction solution under ice cooling to stop the reaction, and separation was then carried out. The organic layer was washed five times with a 7% aqueous sodium hydrogencarbonate solution. The solvent was evaporated under reduced pressure. Diethyl ether and water were added to the residue. The organic layer after the separation was successively washed twice with water, with 0.5 M hydrochloric acid, twice with water, and then with 20% saline. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane) to give a crude product of ethyl 2-(1-(1,3-diethoxy-2-propoxycarbonyloxy)-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (1.15 g). The temperature was raised to room temperature by stirring for 25 hr the reaction, and separation The organic layer was washed five times with a 7% aqueous sodium hydrogencarbonate solution The solvent was evaporated under reduced pressure Diethyl ether and water were added to the residue The organic layer after the separation was successively washed twice with water, with 0.5 M hydrochloric acid, twice with water The solvent was evaporated under reduced pressure The residue was purified by column chromatography on silica gel (ethyl acetate/hexane)

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

実験手順: To a mixture of Example 58 (500 mg, 2.5 mmol) and pyridine (0.44 ml, 5.5 mmol) in anhydrous dichloromethane (5 ml), at 0° C. and under nitrogen, was added phosgene (20% in toluene, 1.44 ml, 2.75 mmol). The mixture was stirred at 0° C. for 20 min, before addition of 1,3-diethoxypropan-2-ol (407 mg, 2.75 mmol). The reaction mixture was stirred at room temperature for 30 min and then poured into ice water (10 ml). The mixture was adjusted to pH 7 by addition of solid sodium hydrogen carbonate and the two layers were separated. The aqueous phase was extracted with dichloromethane (2×10 ml) and the combined extracts were dried (MgSO4) and concentrated in vacuo. the two layers were separated The aqueous phase was extracted with dichloromethane (2×10 ml) the combined extracts were dried (MgSO4) concentrated in vacuo

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

実験手順: To a mixture of Example 58 (500 mg, 2.5 mmol) and pyridine (0.44 ml, 5.5 mmol) in anhydrous dichloromethane (5 ml), at 0° C. and under nitrogen, was added phosgene (20% in toluene, 1.44 ml, 2.75 mmol). The mixture was stirred at 0° C. for 20 min, before addition of 1,3-diethoxypropan-2-ol (407 mg, 2.75 mmol). The reaction mixture was stirred at room temperature for 30 min and then poured into ice water (10 ml). The mixture was adjusted to pH 7 by addition of solid sodium hydrogen carbonate and the two layers were separated. The aqueous phase was extracted with dichloromethane (2×10 ml) and the combined extracts were dried (MgSO4) and concentrated in vacuo. the two layers were separated The aqueous phase was extracted with dichloromethane (2×10 ml) the combined extracts were dried (MgSO4) concentrated in vacuo

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

実験手順: To a mixture of Example 58 (500 mg, 2.5 mmol) and pyridine (0.44 ml, 5.5 mmol) in anhydrous dichloromethane (5 ml), at 0° C. and under nitrogen, was added phosgene (20% in toluene, 1.44 ml, 2.75 mmol). The mixture was stirred at 0° C. for 20 min, before addition of 1,3-diethoxypropan-2-ol (407 mg, 2.75 mmol). The reaction mixture was stirred at room temperature for 30 min and then poured into ice water (10 ml). The mixture was adjusted to pH 7 by addition of solid sodium hydrogen carbonate and the two layers were separated. The aqueous phase was extracted with dichloromethane (2×10 ml) and the combined extracts were dried (MgSO4) and concentrated in vacuo. the two layers were separated The aqueous phase was extracted with dichloromethane (2×10 ml) the combined extracts were dried (MgSO4) concentrated in vacuo

反応条件: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: p-Toluenesulfonic acid monohydrate (57 mg) and isobutyl aldehyde (0.41 ml) were added to a solution of ethyl 5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (1.14 g), prepared in step (32a), in methylene chloride solution (17 ml) at −20° C. The mixture was stirred at that temperature for one hr. 1,1′-Carbonyldiimidazole (732 mg) was added to the reaction solution. Further, one hr after that, 1,3-diethoxy-2-propanol (4.70 ml) was added thereto. The reaction solution was cooled to −30° C. Trifluoroacetic acid (0.70 ml) was added thereto. The temperature was raised to room temperature, followed by stirring for 25 hr. 0.5 M hydrochloric acid was added to the reaction solution under ice cooling to stop the reaction, and separation was then carried out. The organic layer was washed five times with a 7% aqueous sodium hydrogencarbonate solution. The solvent was evaporated under reduced pressure. Diethyl ether and water were added to the residue. The organic layer after the separation was successively washed twice with water, with 0.5 M hydrochloric acid, twice with water, and then with 20% saline. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane) to give a crude product of ethyl 2-(1-(1,3-diethoxy-2-propoxycarbonyloxy)-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (1.15 g). The temperature was raised to room temperature by stirring for 25 hr the reaction, and separation The organic layer was washed five times with a 7% aqueous sodium hydrogencarbonate solution The solvent was evaporated under reduced pressure Diethyl ether and water were added to the residue The organic layer after the separation was successively washed twice with water, with 0.5 M hydrochloric acid, twice with water The solvent was evaporated under reduced pressure The residue was purified by column chromatography on silica gel (ethyl acetate/hexane)

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

実験手順: 2-{[({[(tert-Butoxy)carbonyl]amino}oxy)carbonyl]oxy}-1,3-diethoxypropane is prepared from tert-butyl N-hydroxycarbamate and 1,3-diethoxypropan-2-ol using 20% solution of phosgene in toluene according to Scheme 10. (10.37 g, 85%), 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.73 (1H, s), 5.03 (1H, quin, 5.2 Hz), 3.64 (4H, dd, 5.1, 2.7 Hz), 3.48-3.57 (4H, m), 1.50 (9H, s), 1.19 (6H, t, 7.0 Hz).

反応条件: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: p-Toluenesulfonic acid monohydrate (57 mg) and isobutyl aldehyde (0.41 ml) were added to a solution of ethyl 5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (1.14 g), prepared in step (32a), in methylene chloride solution (17 ml) at −20° C. The mixture was stirred at that temperature for one hr. 1,1′-Carbonyldiimidazole (732 mg) was added to the reaction solution. Further; one hr after that, 1,3-diethoxy-2-propanol (4.70 ml) was added thereto. The reaction solution was cooled to −30° C. Trifluoroacetic acid (0.70 ml) was added thereto. The temperature was raised to room temperature, followed by stirring for 25 hr. 0.5 M hydrochloric acid was added to the reaction solution under ice cooling to stop the reaction, and separation was then carried out. The organic layer was washed five times with a 7% aqueous sodium hydrogencarbonate solution. The solvent was evaporated under reduced pressure. Diethyl ether and water were added to the residue. The organic layer after the separation was successively washed twice with water, with 0.5 M hydrochloric acid, twice with water, and then with 20% saline. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane) to give a crude product of ethyl 2-(1-(1,3-diethoxy-2-propoxycarbonyloxy)-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (1.15 g). The temperature was raised to room temperature by stirring for 25 hr the reaction, and separation The organic layer was washed five times with a 7% aqueous sodium hydrogencarbonate solution The solvent was evaporated under reduced pressure Diethyl ether and water were added to the residue The organic layer after the separation was successively washed twice with water, with 0.5 M hydrochloric acid, twice with water The solvent was evaporated under reduced pressure The residue was purified by column chromatography on silica gel (ethyl acetate/hexane)

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

実験手順: The same operation as in Example 1-1 or 1-2 was carried out using trans-2-decenoic acid and 1,3-diethoxy-2-propanol as starting materials to give the aimed compound.

反応条件: temp:-30.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: p-Toluenesulfonic acid monohydrate (57 mg) and isobutyl aldehyde (0.41 ml) were added to a solution of ethyl 5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (1.14 g), prepared in step (32a), in methylene chloride solution (17 ml) at −20° C. The mixture was stirred at that temperature for one hr. 1,1′-Carbonyldiimidazole (732 mg) was added to the reaction solution. Further, one hr after that, 1,3-diethoxy-2-propanol (4.70 ml) was added thereto. The reaction solution was cooled to −30° C. Trifluoroacetic acid (0.70 ml) was added thereto. The temperature was raised to room temperature, followed by stirring for 25 hr. 0.5 M hydrochloric acid was added to the reaction solution under ice cooling to stop the reaction, and separation was then carried out. The organic layer was washed five times with a 7% aqueous sodium hydrogencarbonate solution. The solvent was evaporated under reduced pressure. Diethyl ether and water were added to the residue. The organic layer after the separation was successively washed twice with water, with 0.5 M hydrochloric acid, twice with water, and then with 20% saline. The solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane) to give a crude product of ethyl 2-(1-(1,3-diethoxy-2-propoxycarbonyloxy)-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (1.15 g). The temperature was raised to room temperature by stirring for 25 hr the reaction, and separation The organic layer was washed five times with a 7% aqueous sodium hydrogencarbonate solution The solvent was evaporated under reduced pressure Diethyl ether and water were added to the residue The organic layer after the separation was successively washed twice with water, with 0.5 M hydrochloric acid, twice with water The solvent was evaporated under reduced pressure The residue was purified by column chromatography on silica gel (ethyl acetate/hexane)