Ethyl 2-(N-Methoxy-N-methylamino)-2-oxoacetate

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

実験手順: To a solution of N,O-dimethylhydroxylamine hydrochloride (10 g, 102.52 mmol) and ethyl chlorooxoacetate (13.77 ml, 123.02 mmol) in dichloromethane (163 ml) at 0° C. was added triethylamine (28.6 ml, 205.04 mmol) drop wise. The reaction was stirred at room temperature for 1.5 hrs. The reaction was quenched with 20 ml of methanol, and then concentrated. The resulting solid was triturated with THF and filtered away. The filtrate was concentrated. The residue was vacuum distilled bulb to bulb. At approximately 85° C. impurities were collected and then discarded. The title compound was collected at approximately 120° C. as a neat oil (11.6 g, 72.0 mmol, 70.2%). The reaction was quenched with 20 ml of methanol concentrated The resulting solid was triturated with THF filtered away The filtrate was concentrated distilled bulb to bulb At approximately 85° C. impurities were collected

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

実験手順: To a solution of N,O-dimethylhydroxylamine hydrochloride (10 g, 102.52 mmol) and ethyl chlorooxoacetate (13.77 ml, 123.02 mmol) in dichloromethane (163 ml) at 0° C. was added triethylamine (28.6 ml, 205.04 mmol) drop wise. The reaction was stirred at room temperature for 1.5 hrs. The reaction was quenched with 20 ml of methanol, and then concentrated. The resulting solid was triturated with THF and filtered away. The filtrate was concentrated. The residue was vacuum distilled bulb to bulb. At approximately 85° C. impurities were collected and then discarded. The title compound was collected at approximately 120° C. as a neat oil (11.6 g, 72.0 mmol, 70.2%). The reaction was quenched with 20 ml of methanol concentrated The resulting solid was triturated with THF filtered away The filtrate was concentrated distilled bulb to bulb At approximately 85° C. impurities were collected

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

実験手順: Ethyloxalyl chloride (15.2 g, 92.7 mmol) and N,O-dimethylhydroxylamine hydrochloride (9.00 g, 92.3 mmol) were added to chloroform (180 ml) at 0° C. To the mixture was gradually added triethylamine (18.6 g, 184 mmol) under stirring. After the mixture was allowed to warm up to room temperature, the mixture was stirred for 30 minutes, and then methanol (30 ml) was added thereto. The reaction solution was concentrated in vacuo to give a residue, to which was added tetrahydrofuran. The resulting precipitates were filtered off, and the filtrate was concentrated. The residue was distilled to give the title compound (7.47 g) as a pale yellow oil. the mixture was stirred for 30 minutes The reaction solution was concentrated in vacuo to give a residue The resulting precipitates were filtered off the filtrate was concentrated The residue was distilled

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

実験手順: Ethyloxalyl chloride (15.2 g, 92.7 mmol) and N,O-dimethylhydroxylamine hydrochloride (9.00 g, 92.3 mmol) were added to chloroform (180 ml) at 0° C. To the mixture was gradually added triethylamine (18.6 g, 184 mmol) under stirring. After the mixture was allowed to warm up to room temperature, the mixture was stirred for 30 minutes, and then methanol (30 ml) was added thereto. The reaction solution was concentrated in vacuo to give a residue, to which was added tetrahydrofuran. The resulting precipitates were filtered off, and the filtrate was concentrated. The residue was distilled to give the title compound (7.47 g) as a pale yellow oil. the mixture was stirred for 30 minutes The reaction solution was concentrated in vacuo to give a residue The resulting precipitates were filtered off the filtrate was concentrated The residue was distilled

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

実験手順: Ethyloxalyl chloride (15.2 g, 92.7 mmol) and N,O-dimethylhydroxylamine hydrochloride (9.00 g, 92.3 mmol) were added to chloroform (180 ml) at 0° C. To the mixture was gradually added triethylamine (18.6 g, 184 mmol) under stirring. After the mixture was allowed to warm up to room temperature, the mixture was stirred for 30 minutes, and then methanol (30 ml) was added thereto. The reaction solution was concentrated in vacuo to give a residue, to which was added tetrahydrofuran. The resulting precipitates were filtered off, and the filtrate was concentrated. The residue was distilled to give the title compound (7.47 g) as a pale yellow oil. the mixture was stirred for 30 minutes The reaction solution was concentrated in vacuo to give a residue The resulting precipitates were filtered off the filtrate was concentrated The residue was distilled

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

実験手順: To a solution of N,O-dimethylhydroxylamine hydrochloride (10 g, 102.52 mmol) and ethyl chlorooxoacetate (13.77 ml, 123.02 mmol) in dichloromethane (163 ml) at 0° C. was added triethylamine (28.6 ml, 205.04 mmol) drop wise. The reaction was stirred at room temperature for 1.5 hrs. The reaction was quenched with 20 ml of methanol, and then concentrated. The resulting solid was triturated with THF and filtered away. The filtrate was concentrated. The residue was vacuum distilled bulb to bulb. At approximately 85° C. impurities were collected and then discarded. The title compound was collected at approximately 120° C. as a neat oil (11.6 g, 72.0 mmol, 70.2%). The reaction was quenched with 20 ml of methanol concentrated The resulting solid was triturated with THF filtered away The filtrate was concentrated distilled bulb to bulb At approximately 85° C. impurities were collected

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

実験手順: To a solution of N,O-dimethylhydroxylamine hydrochloride (10 g, 102.52 mmol) and ethyl chlorooxoacetate (13.77 ml, 123.02 mmol) in dichloromethane (163 ml) at 0° C. was added triethylamine (28.6 ml, 205.04 mmol) drop wise. The reaction was stirred at room temperature for 1.5 hrs. The reaction was quenched with 20 ml of methanol, and then concentrated. The resulting solid was triturated with THF and filtered away. The filtrate was concentrated. The residue was vacuum distilled bulb to bulb. At approximately 85° C. impurities were collected and then discarded. The title compound was collected at approximately 120° C. as a neat oil (11.6 g, 72.0 mmol, 70.2%). The reaction was quenched with 20 ml of methanol concentrated The resulting solid was triturated with THF filtered away The filtrate was concentrated distilled bulb to bulb At approximately 85° C. impurities were collected

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

実験手順: To a solution of N,O-dimethylhydroxylamine hydrochloride (10 g, 102.52 mmol) and ethyl chlorooxoacetate (13.77 ml, 123.02 mmol) in dichloromethane (163 ml) at 0° C. was added triethylamine (28.6 ml, 205.04 mmol) drop wise. The reaction was stirred at room temperature for 1.5 hrs. The reaction was quenched with 20 ml of methanol, and then concentrated. The resulting solid was triturated with THF and filtered away. The filtrate was concentrated. The residue was vacuum distilled bulb to bulb. At approximately 85° C. impurities were collected and then discarded. The title compound was collected at approximately 120° C. as a neat oil (11.6 g, 72.0 mmol, 70.2%). The reaction was quenched with 20 ml of methanol concentrated The resulting solid was triturated with THF filtered away The filtrate was concentrated distilled bulb to bulb At approximately 85° C. impurities were collected

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

実験手順: Ethyloxalyl chloride (15.2 g, 92.7 mmol) and N,O-dimethylhydroxylamine hydrochloride (9.00 g, 92.3 mmol) were added to chloroform (180 ml) at 0° C. To the mixture was gradually added triethylamine (18.6 g, 184 mmol) under stirring. After the mixture was allowed to warm up to room temperature, the mixture was stirred for 30 minutes, and then methanol (30 ml) was added thereto. The reaction solution was concentrated in vacuo to give a residue, to which was added tetrahydrofuran. The resulting precipitates were filtered off, and the filtrate was concentrated. The residue was distilled to give the title compound (7.47 g) as a pale yellow oil. the mixture was stirred for 30 minutes The reaction solution was concentrated in vacuo to give a residue The resulting precipitates were filtered off the filtrate was concentrated The residue was distilled

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

実験手順: Ethyloxalyl chloride (15.2 g, 92.7 mmol) and N,O-dimethylhydroxylamine hydrochloride (9.00 g, 92.3 mmol) were added to chloroform (180 ml) at 0° C. To the mixture was gradually added triethylamine (18.6 g, 184 mmol) under stirring. After the mixture was allowed to warm up to room temperature, the mixture was stirred for 30 minutes, and then methanol (30 ml) was added thereto. The reaction solution was concentrated in vacuo to give a residue, to which was added tetrahydrofuran. The resulting precipitates were filtered off, and the filtrate was concentrated. The residue was distilled to give the title compound (7.47 g) as a pale yellow oil. the mixture was stirred for 30 minutes The reaction solution was concentrated in vacuo to give a residue The resulting precipitates were filtered off the filtrate was concentrated The residue was distilled

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

実験手順: To a solution of N,O-dimethylhydroxylamine hydrochloride (10 g, 102.52 mmol) and ethyl chlorooxoacetate (13.77 ml, 123.02 mmol) in dichloromethane (163 ml) at 0° C. was added triethylamine (28.6 ml, 205.04 mmol) drop wise. The reaction was stirred at room temperature for 1.5 hrs. The reaction was quenched with 20 ml of methanol, and then concentrated. The resulting solid was triturated with THF and filtered away. The filtrate was concentrated. The residue was vacuum distilled bulb to bulb. At approximately 85° C. impurities were collected and then discarded. The title compound was collected at approximately 120° C. as a neat oil (11.6 g, 72.0 mmol, 70.2%). The reaction was quenched with 20 ml of methanol concentrated The resulting solid was triturated with THF filtered away The filtrate was concentrated distilled bulb to bulb At approximately 85° C. impurities were collected

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

実験手順: To a solution of N,O-dimethylhydroxylamine hydrochloride (10 g, 102.52 mmol) and ethyl chlorooxoacetate (13.77 ml, 123.02 mmol) in dichloromethane (163 ml) at 0° C. was added triethylamine (28.6 ml, 205.04 mmol) drop wise. The reaction was stirred at room temperature for 1.5 hrs. The reaction was quenched with 20 ml of methanol, and then concentrated. The resulting solid was triturated with THF and filtered away. The filtrate was concentrated. The residue was vacuum distilled bulb to bulb. At approximately 85° C. impurities were collected and then discarded. The title compound was collected at approximately 120° C. as a neat oil (11.6 g, 72.0 mmol, 70.2%). The reaction was quenched with 20 ml of methanol concentrated The resulting solid was triturated with THF filtered away The filtrate was concentrated distilled bulb to bulb At approximately 85° C. impurities were collected