2-[ethyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]acetic acid

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

Procedure: To a 3° C. solution of 86 g (423 mmole) of N-[(1,1-dimethylethoxy)carbonyl]-N-ethylglycine, 21.4 g (465 mmole) of ethanol and 5.17 g (42.3 mmole) of 4-dimethylaminopyridine in 600 mL of dichloromethane is added 47 g (46.2 mmole) of triethylamine, followed by portionwise addition of 89.1 g (46.5 mmole) of 3-N,N-dimethylaminopropylethylcarbodiimide hydrochloride. The stirred mixture is allowed to warm to ambient temperature and stir overnight. The reaction mixture is washed with water, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give N-[(1,1-dimethylethoxy)carbonyl]-N-ethylglycine ethyl ester (88 g) as an oil. MS (FAB) 232 (M+H)+. The reaction mixture is washed with water, saturated aqueous sodium bicarbonate and brine dried over magnesium sulfate filtered concentrated in vacuo

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

Procedure: To a 3° C. solution of 86 g (423 mmole) of N-[(1,1-dimethylethoxy)carbonyl]-N-ethylglycine, 21.4 g (465 mmole) of ethanol and 5.17 g (42.3 mmole) of 4-dimethylaminopyridine in 600 mL of dichloromethane is added 47 g (46.2 mmole) of triethylamine, followed by portionwise addition of 89.1 g (46.5 mmole) of 3-N,N-dimethylaminopropylethylcarbodiimide hydrochloride. The stirred mixture is allowed to warm to ambient temperature and stir overnight. The reaction mixture is washed with water, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give N-[(1,1-dimethylethoxy)carbonyl]-N-ethylglycine ethyl ester (88 g) as an oil. MS (FAB) 232 (M+H)+. The reaction mixture is washed with water, saturated aqueous sodium bicarbonate and brine dried over magnesium sulfate filtered concentrated in vacuo

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

Procedure: To a 3° C. solution of 86 g (423 mmole) of N-[(1,1-dimethylethoxy)carbonyl]-N-ethylglycine, 21.4 g (465 mmole) of ethanol and 5.17 g (42.3 mmole) of 4-dimethylaminopyridine in 600 mL of dichloromethane is added 47 g (46.2 mmole) of triethylamine, followed by portionwise addition of 89.1 g (46.5 mmole) of 3-N,N-dimethylaminopropylethylcarbodiimide hydrochloride. The stirred mixture is allowed to warm to ambient temperature and stir overnight. The reaction mixture is washed with water, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to give N-[(1,1-dimethylethoxy)carbonyl]-N-ethylglycine ethyl ester (88 g) as an oil. MS (FAB) 232 (M+H)+. The reaction mixture is washed with water, saturated aqueous sodium bicarbonate and brine dried over magnesium sulfate filtered concentrated in vacuo