methyl 2-[(2-methoxy-2-oxoethyl)amino]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:

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

Procedure: A solution of 1.9 g (4.78 mmol) of 3-(octadecyloxy)phenylacetic acid in 40 ml of thionyl chloride was refluxed for 1.5 hours. The excess thionyl chloride was removed at reduced pressure and the resultant acid chloride was dissolved in 40 ml of anhydrous methylene chloride. This solution was added dropwise to an ice bath cooled mixture of 1.0 g (6 mmol) of dimethyl iminodiacetate and 1.4 ml (10 mmol) of triethylamine in 25 ml of methylene chloride. The reaction mixture was kept at room temperature for 17 hours and then was washed with 1N HCl, dried and concentrated to a solid. Purification by chromatography on 150 g of silica gel using 40% ethyl acetate-hexane gave 1.7 g (65% yield, mp 52°-55°) of N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)phenylacetyl]glycine methyl ester. The excess thionyl chloride was removed at reduced pressure the resultant acid chloride was dissolved in 40 ml of anhydrous methylene chloride This solution was added dropwise to an ice bath cooled was washed with 1N HCl dried concentrated to a solid Purification by chromatography on 150 g of silica gel using 40% ethyl acetate-hexane

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

Procedure: A solution of 0.8 g (1.46 mmol) of 3,4-bis(tetradecyloxy)benzoic acid and 20 ml of thionyl chloride was stirred at reflux for 3 hours. The excess thionyl chloride was removed at reduced pressure and the resultant acid chloride was dissolved in 10 ml of methylene chloride and 10 ml of anhydrous THF. This solution was added dropwise to a stirred, ice cooled mixture of 0.3 ml (1.86 mmol) of dimethyl iminodiacetate and 0.41 ml (2.9 mmol) of triethylamine in 10 ml of anhydrous methylene chloride. The cooling bath was removed after 30 minutes and the mixture was left at room temperature for 18 hours. The solvents were removed at reduced pressure and the residue was extracted with ethyl acetate. The extract was washed successively with 1N HCl, with NaHCO3 solution, dried and concentrated. Crystallization from ethyl acetate-hexane gave 0.905 g (90% yield, mp 70°-71°) of N-(2-methoxy-2-oxoethyl)-N-[3,4-bis(tetradecyloxy)benzoyl]glycine methyl ester. at reflux for 3 hours The excess thionyl chloride was removed at reduced pressure the resultant acid chloride was dissolved in 10 ml of methylene chloride This solution was added dropwise to a stirred, ice cooled The cooling bath was removed after 30 minutes The solvents were removed at reduced pressure the residue was extracted with ethyl acetate The extract was washed successively with 1N HCl, with NaHCO3 solution dried concentrated Crystallization from ethyl acetate-hexane

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

Procedure: Conversion of 3-nitro-5-(octadecyloxy)benzoic acid to the acid chloride with thionyl chloride followed by treatment with dimethyl iminodiacetate gave a 79% yield of N-(2-methoxy-2-oxoethyl)-N-[3-nitro-5-(octadecyloxy)benzoyl]glycine methyl ester as an oil after chromatography on silica gel using 25% ethyl acetate-hexane. The nmr spectrum was consistent with the structure.

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

Procedure: Conversion of 3-(octadecyloxy)-5-(phenylmethoxy)benzoic acid to the acid chloride with thionyl chloride followed by treatment with dimethyl iminodiacetate gave N-(2-methoxy-2-oxoethyl)-N-[3-(octadecyloxy)-5-(phenylmethoxy)benzoyl]glycine methyl ester as an oil after chromatography on 50 g of silica gel using 25% ethyl acetate-hexane. The structure was confirmed by the nmr spectrum.

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

Procedure: The reaction of 3,5-bis(tetradecyloxy)benzoyl chloride with dimethyl iminodiacetate as in Example 10 gave N-[3,5-bis (tetradecyloxy)benzoyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester as an oil. The nmr and mass spectra were consistent with the structure.

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

Procedure: The reaction of 3,5-bis(tetradecyloxy)benzoyl chloride with dimethyl iminodiacetate as in Example 10 gave N-[3,5-bis (tetradecyloxy)benzoyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester as an oil. The nmr and mass spectra were consistent with the structure.

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

Procedure: The conversion of 3-(decyloxy)benzoic acid to the acid chloride followed by treatment with dimethyl iminodiacetate as in Example 1 gave N-(2-methoxy-2-oxoethyl)-N-[3-(decyloxy)benzoyl]glycine methyl ester as an oil. The nmr and mass spectra were consistent with the structure.

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

Procedure: The conversion of 3-(tetradecyloxy)benzoic acid to the acid chloride followed by treatment with dimethyl iminodiacetate as in Example 1 gave N-(2-methoxy-2-oxoethyl)-N-[3-(tetradecyloxy)benzoyl]glycine methyl ester, mp <23°. The nmr and mass spectra were consistent with the structure.