ethyl 2-cyano-2-(phenylmethoxycarbonylamino)acetate

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

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of ethyl 2-cyano-2-hydroxyiminoacetate (100 g, 0.704 mol) and water (600 ml), were added a saturated aqueous solution of sodium bicarbonate (200 ml) and sodium hydrosulfite (340 g, 1.96 mol) under ice-cooling, and then benzyloxycarbonyl chloride (144 g, 0.848 mol) was added dropwise under ice-cooling. After the addition was completed, the reaction solution was stirred at 20-30° C. for about 4 hours. Completion of the reaction was confirmed using TLC shown below, precipitated crystals were collected by filtration and washed with sprayed water (50 ml×3). The obtained crystals were recrystallized from ethanol (600 ml), filtered and washed with sprayed ethanol (50 ml×3), dried in airflow at 40° C. to give ethyl 2-benzyloxycarbonylamino-2-cyanoacetate (118.7 g, yield 64.2%). cooling cooling After the addition precipitated crystals were collected by filtration washed with sprayed water (50 ml×3) The obtained crystals were recrystallized from ethanol (600 ml) filtered washed with sprayed ethanol (50 ml×3) dried in airflow at 40° C.

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a sodium ethoxide solution, which was prepared from sodium (2.11 g) and ethanol (400 ml), were added in turn 2-benzyloxycarbonylamino-2-cyanoacetic acid ethyl ester (24.0 g) and ethyl bromoacetate (15.3 g). The resulting mixture was stirred at 25° C. for 3 hours and concentrated under reduced pressure. The residue was diluted with water and extracted with chloroform. The extracts were washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give the title compound (31.6 g, 99%) as a colorless oil. concentrated under reduced pressure The residue was diluted with water extracted with chloroform The extracts were washed with water dried over anhydrous sodium sulfate evaporated under reduced pressure

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a sodium ethoxide solution, which was prepared from sodium (2.11 g) and ethanol (400 ml), were added in turn 2-benzyloxycarbonylamino-2-cyanoacetic acid ethyl ester (24.0 g) and ethyl bromoacetate (15.3 g). The resulting mixture was stirred at 25° C. for 3 hours and concentrated under reduced pressure. The residue was diluted with water and extracted with chloroform. The extracts were washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give the title compound (31.6 g, 99%) as a colorless oil. concentrated under reduced pressure The residue was diluted with water extracted with chloroform The extracts were washed with water dried over anhydrous sodium sulfate evaporated under reduced pressure

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

Procedure: To a stirred mixture of 2-amino-2-cyanoacetic acid ethyl ester (19.7 g) and pyridine (12.2 g) in water (123 ml) was added portionwise benzyloxycarbonyl chloride (27.9 g) under ice cooling. The resulting mixture was stirred under ice cooling for 1 hour. Precipitated crystals were collected, washed thoroughly with water, and recrystallized from ethanol to give the title compound (24.2 g, 60.2%) as colorless crystals, mp 111°-112° C. Precipitated crystals were collected washed thoroughly with water recrystallized from ethanol

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

Procedure: To a stirred mixture of 2-amino-2-cyanoacetic acid ethyl ester (19.7 g) and pyridine (12.2 g) in water (123 ml) was added portionwise benzyloxycarbonyl chloride (27.9 g) under ice cooling. The resulting mixture was stirred under ice cooling for 1 hour. Precipitated crystals were collected, washed thoroughly with water, and recrystallized from ethanol to give the title compound (24.2 g, 60.2%) as colorless crystals, mp 111°-112° C. Precipitated crystals were collected washed thoroughly with water recrystallized from ethanol

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of ethyl 2-cyano-2-hydroxyiminoacetate (100 g, 0.704 mol) and water (600 ml), were added a saturated aqueous solution of sodium bicarbonate (200 ml) and sodium hydrosulfite (340 g, 1.96 mol) under ice-cooling, and then benzyloxycarbonyl chloride (144 g, 0.848 mol) was added dropwise under ice-cooling. After the addition was completed, the reaction solution was stirred at 20-30° C. for about 4 hours. Completion of the reaction was confirmed using TLC shown below, precipitated crystals were collected by filtration and washed with sprayed water (50 ml×3). The obtained crystals were recrystallized from ethanol (600 ml), filtered and washed with sprayed ethanol (50 ml×3), dried in airflow at 40° C. to give ethyl 2-benzyloxycarbonylamino-2-cyanoacetate (118.7 g, yield 64.2%). cooling cooling After the addition precipitated crystals were collected by filtration washed with sprayed water (50 ml×3) The obtained crystals were recrystallized from ethanol (600 ml) filtered washed with sprayed ethanol (50 ml×3) dried in airflow at 40° C.

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a sodium ethoxide solution, which was prepared from sodium (2.11 g) and ethanol (400 ml), were added in turn 2-benzyloxycarbonylamino-2-cyanoacetic acid ethyl ester (24.0 g) and ethyl bromoacetate (15.3 g). The resulting mixture was stirred at 25° C. for 3 hours and concentrated under reduced pressure. The residue was diluted with water and extracted with chloroform. The extracts were washed with water, dried over anhydrous sodium sulfate, and evaporated under reduced pressure to give the title compound (31.6 g, 99%) as a colorless oil. concentrated under reduced pressure The residue was diluted with water extracted with chloroform The extracts were washed with water dried over anhydrous sodium sulfate evaporated under reduced pressure

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

Procedure: To a stirred mixture of 2-amino-2-cyanoacetic acid ethyl ester (19.7 g) and pyridine (12.2 g) in water (123 ml) was added portionwise benzyloxycarbonyl chloride (27.9 g) under ice cooling. The resulting mixture was stirred under ice cooling for 1 hour. Precipitated crystals were collected, washed thoroughly with water, and recrystallized from ethanol to give the title compound (24.2 g, 60.2%) as colorless crystals, mp 111°-112° C. Precipitated crystals were collected washed thoroughly with water recrystallized from ethanol

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

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of ethyl 2-cyano-2-hydroxyiminoacetate (100 g, 0.704 mol) and water (600 ml), were added a saturated aqueous solution of sodium bicarbonate (200 ml) and sodium hydrosulfite (340 g, 1.96 mol) under ice-cooling, and then benzyloxycarbonyl chloride (144 g, 0.848 mol) was added dropwise under ice-cooling. After the addition was completed, the reaction solution was stirred at 20-30° C. for about 4 hours. Completion of the reaction was confirmed using TLC shown below, precipitated crystals were collected by filtration and washed with sprayed water (50 ml×3). The obtained crystals were recrystallized from ethanol (600 ml), filtered and washed with sprayed ethanol (50 ml×3), dried in airflow at 40° C. to give ethyl 2-benzyloxycarbonylamino-2-cyanoacetate (118.7 g, yield 64.2%). cooling cooling After the addition precipitated crystals were collected by filtration washed with sprayed water (50 ml×3) The obtained crystals were recrystallized from ethanol (600 ml) filtered washed with sprayed ethanol (50 ml×3) dried in airflow at 40° C.

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of ethyl 2-cyano-2-hydroxyiminoacetate (100 g, 0.704 mol) and water (600 ml), were added a saturated aqueous solution of sodium bicarbonate (200 ml) and sodium hydrosulfite (340 g, 1.96 mol) under ice-cooling, and then benzyloxycarbonyl chloride (144 g, 0.848 mol) was added dropwise under ice-cooling. After the addition was completed, the reaction solution was stirred at 20-30° C. for about 4 hours. Completion of the reaction was confirmed using TLC shown below, precipitated crystals were collected by filtration and washed with sprayed water (50 ml×3). The obtained crystals were recrystallized from ethanol (600 ml), filtered and washed with sprayed ethanol (50 ml×3), dried in airflow at 40° C. to give ethyl 2-benzyloxycarbonylamino-2-cyanoacetate (118.7 g, yield 64.2%). cooling cooling After the addition precipitated crystals were collected by filtration washed with sprayed water (50 ml×3) The obtained crystals were recrystallized from ethanol (600 ml) filtered washed with sprayed ethanol (50 ml×3) dried in airflow at 40° C.