ethyl 2-[(2-chloroacetyl)amino]acetate

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: The ester prepared in step 1 is reacted with chloroacetylchloride at a temperature of from about -10° to +10° C. in a suitable solvent in the presence of a suitable base to produce chloroacetylglycine ethyl ester. Solvents useful in this reaction include water, dichloromethane, and dichloroethane. Suitable bases include sodium bicarbonate, sodium carbonate, potassium carbonate, and sodium hydroxide. If the aminoacid is used in the form of its hydrochloride, a two-fold excess of base must be used.

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of 4-hydroxybenzaldehyde (6.1 g), potassium carbonate (13.8 g), sodium iodide (0.75 g) and N,N-dimethylformamide (110 ml) was added N-(ethoxycarbonylmethyl)-2-chloroacetamide (8.9 g), and the mixture was stirred at 80° C. for 30 minutes. The reaction mixture was poured into 3% hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was chromatographed on silica gel column (eluent; ethyl acetate), the desired fractions were collected and recrystallized from ethyl acetate/hexane to give N-(ethoxycarbonylmethyl)-2-(4-formylphenoxy)acetamide (4.09 g). extracted with ethyl acetate The ethyl acetate layer was washed successively with water a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate After evaporation of the solvent under reduced pressure the residue was chromatographed on silica gel column (eluent; ethyl acetate) the desired fractions were collected recrystallized from ethyl acetate/hexane

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

実験手順: Twenty-seven and nine-tenths grams (g) (0.2 mole) of glycine ethyl ester --HCl was combined with about 100 grams of ice in a reaction flask. Solid NaHCO3 (33.6 g) (0.4 mole) was then added to this mixture followed by dropwise addition of 23.0 g (0.2 mole) of chloroacetyl chloride with stirring. The temperature of the reaction mixture was maintained between -10° and -5° C. by ice addition. The solid precipitate that formed was separated from the reaction mixture by filtration, washed with ice water and air dried. The yield was 15 g (41.7%) of a solid having a melting point of 60°-62° C. which was identified as the title compound by infrared (IR) spectroscopy analysis. The temperature of the reaction mixture was maintained between -10° and -5° C. by ice addition The solid precipitate that formed was separated from the reaction mixture by filtration washed with ice water and air dried

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of 4-hydroxybenzaldehyde (6.1 g), potassium carbonate (13.8 g), sodium iodide (0.75 g) and dimethylformamide (110 ml) was added N-(ethoxycarbonylmethyl)-2-chloroacetamide (8.9 g), and the mixture was stirred at 80° C. for 30 minutes. The reaction mixture was poured into 3% hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was chromatographed on silica gel column (eluent; ethyl acetate), the desired fractions were collected and recrystallized from ethyl acetate/hexane to give N-(ethoxycarbonylmethyl)-2-(4-formylphenoxy)acetamide (4.09 g). extracted with ethyl acetate The ethyl acetate layer was washed successively with water a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate After evaporation of the solvent under reduced pressure the residue was chromatographed on silica gel column (eluent; ethyl acetate) the desired fractions were collected recrystallized from ethyl acetate/hexane

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

実験手順: The ester prepared in step 1 is reacted with chloroacetylchloride at a temperature of from about -10° to +10° C. in a suitable solvent in the presence of a suitable base to produce chloroacetylglycine ethyl ester. Solvents useful in this reaction include water, dichloromethane, and dichloroethane. Suitable bases include sodium bicarbonate, sodium carbonate, potassium carbonate, and sodium hydroxide. If the aminoacid is used in the form of its hydrochloride, a two-fold excess of base must be used.

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a mixture of 4-hydroxybenzaldehyde (6.1 g), potassium carbonate (13.8 g), sodium iodide (0.75 g) and N,N-dimethylformamide (110 ml) was added N-(ethoxycarbonylmethyl)-2-chloroacetamide (8.9 g), and the mixture was stirred at 80° C. for 30 minutes. The reaction mixture was poured into 3% hydrochloric acid and extracted with ethyl acetate. The ethyl acetate layer was washed successively with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. After evaporation of the solvent under reduced pressure, the residue was chromatographed on silica gel column (eluent; ethyl acetate), the desired fractions were collected and recrystallized from ethyl acetate/hexane to give N-(ethoxycarbonylmethyl)-2-(4-formylphenoxy)acetamide (4.09 g). extracted with ethyl acetate The ethyl acetate layer was washed successively with water a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate After evaporation of the solvent under reduced pressure the residue was chromatographed on silica gel column (eluent; ethyl acetate) the desired fractions were collected recrystallized from ethyl acetate/hexane