ethyl 2-(phenylmethoxycarbonylamino)acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: At 0° C., 7.0 g (0.05 mol) of H-Gly-OC2H5.HCl, 15 ml of N-ethyl morpholine and 20 g of methylethylphosphinic acid anhydride were added successively to a solution of 10.5 g (0.05 mol) of carbobenzoxy-glycine in 20 ml DMF, while stirring and cooling thoroughly. The mixture was brought to room temperature, while stirring. After 16 hours of standing at room temperature the solvent was distilled off in vacuo, and the residue was dissolved in a mixture of 200 ml of ethyl acetate and 100 ml of a 5% potassium bisulfate solution. The ethyl acetate solution was washed twice with 100 ml each of saturated sodium bicarbonate solution, dried over sodium sulfate and evaporated in vacuo. cooling thoroughly was brought to room temperature while stirring the solvent was distilled off in vacuo the residue was dissolved in a mixture of 200 ml of ethyl acetate and 100 ml of a 5% potassium bisulfate solution The ethyl acetate solution was washed twice with 100 ml each of saturated sodium bicarbonate solution dried over sodium sulfate evaporated in vacuo

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

Procedure: At 0° C., 7.0 g (0.05 mol) of H-Gly-OC2H5.HCl, 15 ml of N-ethyl morpholine and 20 g of methylethylphosphinic acid anhydride were added successively to a solution of 10.5 g (0.05 mol) of carbobenzoxy-glycine in 20 ml DMF, while stirring and cooling thoroughly. The mixture was brought to room temperature, while stirring. After 16 hours of standing at room temperature the solvent was distilled off in vacuo, and the residue was dissolved in a mixture of 200 ml of ethyl acetate and 100 ml of a 5% potassium bisulfate solution. The ethyl acetate solution was washed twice with 100 ml each of saturated sodium bicarbonate solution, dried over sodium sulfate and evaporated in vacuo. cooling thoroughly was brought to room temperature while stirring the solvent was distilled off in vacuo the residue was dissolved in a mixture of 200 ml of ethyl acetate and 100 ml of a 5% potassium bisulfate solution The ethyl acetate solution was washed twice with 100 ml each of saturated sodium bicarbonate solution dried over sodium sulfate evaporated in vacuo

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

Procedure: Ethyl acrylate (65.01 ml, 600.0 mmol) was added to a toluene (1,200 ml) solution containing N-benzyloxycarbonylglycine ethyl ester (156.3 g, 600.0 mmol) and then, under ice-cooling, sodium hydride (60% oil; 26.40 g, 660.0 mmol) was added thereto. After 10 minutes of stirring at the same temperature, the ice bath was taken off, and the mixture was stirred at room temperature for 20 minutes and then at 50° C. for 3 hours. After completion of the reaction, and under ice-cooling, the reaction solution was adjusted to about pH 3 by adding 10% citric acid aqueous solution and mixed with ethyl acetate, and the mixture was shaken and then subjected to separation of layers. The organic layer was separated and washed with saturated brine, and the water layer was further extracted with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under a reduced pressure to obtain 196.7 g (600.0 mmol, quantitative) of the title compound. under ice-cooling the mixture was stirred at room temperature for 20 minutes at 50° C. for 3 hours After completion of the reaction under ice-cooling the mixture was shaken subjected to separation of layers The organic layer was separated washed with saturated brine the water layer was further extracted with ethyl acetate The organic layers were dried over anhydrous sodium sulfate filtered the solvent was evaporated under a reduced pressure

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

Procedure: Ethyl acrylate (65.01 ml, 600.0 mmol) was added to a toluene (1,200 ml) solution containing N-benzyloxycarbonylglycine ethyl ester (156.3 g, 600.0 mmol) and then, under ice-cooling, sodium hydride (60% oil; 26.40 g, 660.0 mmol) was added thereto. After 10 minutes of stirring at the same temperature, the ice bath was taken off, and the mixture was stirred at room temperature for 20 minutes and then at 50° C. for 3 hours. After completion of the reaction, and under ice-cooling, the reaction solution was adjusted to about pH 3 by adding 10% citric acid aqueous solution and mixed with ethyl acetate, and the mixture was shaken and then subjected to separation of layers. The organic layer was separated and washed with saturated brine, and the water layer was further extracted with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under a reduced pressure to obtain 196.7 g (600.0 mmol, quantitative) of the title compound. under ice-cooling the mixture was stirred at room temperature for 20 minutes at 50° C. for 3 hours After completion of the reaction under ice-cooling the mixture was shaken subjected to separation of layers The organic layer was separated washed with saturated brine the water layer was further extracted with ethyl acetate The organic layers were dried over anhydrous sodium sulfate filtered the solvent was evaporated under a reduced pressure

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

Procedure: Ethyl acrylate (65.01 ml, 600.0 mmol) was added to a toluene (1,200 ml) solution containing N-benzyloxycarbonylglycine ethyl ester (156.3 g, 600.0 mmol) and then, under ice-cooling, sodium hydride (60% oil; 26.40 g, 660.0 mmol) was added thereto. After 10 minutes of stirring at the same temperature, the ice bath was taken off, and the mixture was stirred at room temperature for 20 minutes and then at 50° C. for 3 hours. After completion of the reaction, and under ice-cooling, the reaction solution was adjusted to about pH 3 by adding 10% citric acid aqueous solution and mixed with ethyl acetate, and the mixture was shaken and then subjected to separation of layers. The organic layer was separated and washed with saturated brine, and the water layer was further extracted with ethyl acetate. The organic layers were dried over anhydrous sodium sulfate and then filtered, and the solvent was evaporated under a reduced pressure to obtain 196.7 g (600.0 mmol, quantitative) of the title compound. under ice-cooling the mixture was stirred at room temperature for 20 minutes at 50° C. for 3 hours After completion of the reaction under ice-cooling the mixture was shaken subjected to separation of layers The organic layer was separated washed with saturated brine the water layer was further extracted with ethyl acetate The organic layers were dried over anhydrous sodium sulfate filtered the solvent was evaporated under a reduced pressure

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

Procedure: To a solution of N-benzyloxycarbonylglycine (1.05 g) and triethylamine (0.73 ml) in dimethylformamide (9 ml), 2-ethoxycarbonyloxyimino-2-cyanoacetic acid amide (1.11 g) is added, and the resulting mixture is stirred for 2 hours. The reaction mixture is treated as in Example A to give N-benzyloxycarbonylglycine ethyl ester (0.2 g) as an oil. The reaction mixture is treated as in Example A

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

Procedure: To a solution of N-benzyloxycarbonylglycine (1.05 g) and triethylamine (0.73 ml) in ethyl acetate (10 ml) and tetrahydrofuran (10 ml), 2-ethoxycarbonyloxyimino-2-cyanoacetic acid amide (1.11 g) is added, and the resulting mixture is stirred for 2 hours. The reaction mixture is treated as in Example A to give N-benzyloxycarbonylglycine ethyl ester (1.2 g) as an oil. The reaction mixture is treated as in Example A