N-(2-aminoethyl)-2-(2,6-dichlorophenoxy)propanamide

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: 50.2 g (=0.2646 mols) of titanium tetrachloride are dissolved in a mixture of 700 ml of absolute chloroform and 25 ml of tetrahydrofuran at 0° C. and are mixed with 30.0 g (=0.108 mols) of (+)-2-(2,6 -dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide. A solution of 63.0 g (=0.5155 mols) of 4-dimethylaminopyridine is then added dropwise very slowly at 0° C. with stirring and the mixture is further stirred for 36 hours at room temperature after the solution has been added. After working up and after purification by column chromatography (silica gel-dry column, eluant: chloroform/tetrahydrofuran 3:1), 16.0 g of (+)-2-[1-(2,6-dichlorophenoxy)ethyl]-1,3-diazacyclopent-2-ene C11H12Cl2N2O [259.1], are obtained, Mp: 127°-128° C.: [α]D20 =+80.6° (c=1/ethanol). the mixture is further stirred for 36 hours at room temperature after the solution has been added after purification by column chromatography (silica gel-dry column, eluant: chloroform/tetrahydrofuran 3:1), 16.0 g of (+)-2-[1-(2,6-dichlorophenoxy)ethyl]-1,3-diazacyclopent-2-ene C11H12Cl2N2O [259.1] are obtained

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

実験手順: 42.0 g (=0.160 mols) of (+)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 194.0 g (=3.228 mols) of 1,2-diaminoethane and, after working up, produce 34.0 g of (+)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =+5.6° (c=1/ethanol).

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

実験手順: 58.6 (0.3089 mols) of titanium tetrachloride are dissolved in a mixture of 700 ml of absolute chloroform and 25 ml of tetrahydrofuran at 0° C. and are mixed with 35.0 g (0.1263 mols) of (-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide. A solution of 74.0 g (0.6056 mols) of 4-dimethylaminopyridine is then added dropwise very slowly at 0° C. with stirring and the mixture is further stirred for 36 hours at room temperature after the solution has been added. After working up and after purification by column chromatography (silica gel-dry column, eluant: chloroform/tetrahydrofuran 3:1), 21.0 g of (-)-2-[1-(2,6-dichlorophenoxy)-ethyl]-1,3-diazacyclopent-2-ene C11H12Cl2N2O [259.1], are obtained, Mp.: 126°-127° C.: [α]D20 =-80.2° (c=1/ethanol). the mixture is further stirred for 36 hours at room temperature after the solution has been added after purification by column chromatography (silica gel-dry column, eluant: chloroform/tetrahydrofuran 3:1), 21.0 g of (-)-2-[1-(2,6-dichlorophenoxy)-ethyl]-1,3-diazacyclopent-2-ene C11H12Cl2N2O [259.1] are obtained

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

実験手順: 46.0 g (0.1748 mols) of (-)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 212.0 g (3.527 mols) of 1,2-diaminoethane and, after working up, produce 38.0 g (-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =-5.8° (c=1/ethanol)

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

実験手順: 46.0 g (0.1748 mols) of (-)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 212.0 g (3.527 mols) of 1,2-diaminoethane and, after working up, produce 38.0 g (-)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =-5.8° (c=1/ethanol)

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

実験手順: 50.2 g (=0.2646 mols) of titanium tetrachloride are dissolved in a mixture of 700 ml of absolute chloroform and 25 ml of tetrahydrofuran at 0° C. and are mixed with 30.0 g (=0.108 mols) of (+)-2-(2,6 -dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide. A solution of 63.0 g (=0.5155 mols) of 4-dimethylaminopyridine is then added dropwise very slowly at 0° C. with stirring and the mixture is further stirred for 36 hours at room temperature after the solution has been added. After working up and after purification by column chromatography (silica gel-dry column, eluant: chloroform/tetrahydrofuran 3:1), 16.0 g of (+)-2-[1-(2,6-dichlorophenoxy)ethyl]-1,3-diazacyclopent-2-ene C11H12Cl2N2O [259.1], are obtained, Mp: 127°-128° C.: [α]D20 =+80.6° (c=1/ethanol). the mixture is further stirred for 36 hours at room temperature after the solution has been added after purification by column chromatography (silica gel-dry column, eluant: chloroform/tetrahydrofuran 3:1), 16.0 g of (+)-2-[1-(2,6-dichlorophenoxy)ethyl]-1,3-diazacyclopent-2-ene C11H12Cl2N2O [259.1] are obtained

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

実験手順: 50.2 g (=0.2646 mols) of titanium tetrachloride are dissolved in a mixture of 700 ml of absolute chloroform and 25 ml of tetrahydrofuran at 0° C. and are mixed with 30.0 g (=0.108 mols) of (+)-2-(2,6 -dichlorophenoxy)-propionic acid-N-(2-aminoethyl)-amide. A solution of 63.0 g (=0.5155 mols) of 4-dimethylaminopyridine is then added dropwise very slowly at 0° C. with stirring and the mixture is further stirred for 36 hours at room temperature after the solution has been added. After working up and after purification by column chromatography (silica gel-dry column, eluant: chloroform/tetrahydrofuran 3:1), 16.0 g of (+)-2-[1-(2,6-dichlorophenoxy)ethyl]-1,3-diazacyclopent-2-ene C11H12Cl2N2O [259.1], are obtained, Mp: 127°-128° C.: [α]D20 =+80.6° (c=1/ethanol). the mixture is further stirred for 36 hours at room temperature after the solution has been added after purification by column chromatography (silica gel-dry column, eluant: chloroform/tetrahydrofuran 3:1), 16.0 g of (+)-2-[1-(2,6-dichlorophenoxy)ethyl]-1,3-diazacyclopent-2-ene C11H12Cl2N2O [259.1] are obtained

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

実験手順: 42.0 g (=0.160 mols) of (+)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 194.0 g (=3.228 mols) of 1,2-diaminoethane and, after working up, produce 34.0 g of (+)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =+5.6° (c=1/ethanol).

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

実験手順: 42.0 g (=0.160 mols) of (+)-2-(2,6-dichlorophenoxy)-propionic acid ethylester are stirred for 6 hours at room temperature with 194.0 g (=3.228 mols) of 1,2-diaminoethane and, after working up, produce 34.0 g of (+)-2-(2,6-dichlorophenoxy)-propionic acid-N-(2-aminoethyl)amide, C11H14Cl2N2O2 [277.2] as a high viscosity oil, [α]D20 =+5.6° (c=1/ethanol).

反応条件: temp:0.00; pressure:0.00; stir: