Sodium Iodide → Glycine [[bis(2-hydroxyethyl)amino]carbonyl]methyl ester

A mixture of 1.0 g (1.92 mmol) of N-(carboxymethyl)-N-[3,5-bis(decyloxy)phenyl]glycine, 2.6 ml of N,N-diisopropylethylamine and a solution of N,N-bis(2-hydroxyethyl)-3-chloroacetamide [prepared from the reaction of 2.1 g (20 mmol) of diethanolamine, 1.6 ml (20 mmol) of chloroacetyl chloride and 3.1 ml (22 mmol) of triethylamine in 25 ml of DMF] was stirred at room temperature for 17 hours. Sodium iodide (3.0 g, 20 mmol) was added and the reaction mixture was stired and heated at 60° under argon for 25 hours. The mixture was concentrated at reduced pressure and NaHCO3 solution was added to the residue. The product was extracted with ethyl acetate and the extract was washed with water, dried and concentrated to an oil which was crystallized from methylene chloride-ether to give 0.455 g (29% yield, mp 104°-107°) of N-[3,5-bis(decyloxy)phenyl]-N-[[bis(2-hydroxyethyl)amino]carbonyl]methoxy]-2-oxoethyl]glycine [[bis(2-hydroxyethyl)amino]carbonyl]methyl ester.

1. temperatureheated at 60° under argon for 25 hours
2. concentrationThe mixture was concentrated at reduced pressure and NaHCO3 solution
3. additionwas added to the residue
4. extractionThe product was extracted with ethyl acetate
5. washthe extract was washed with water
6. customdried
7. concentrationconcentrated to an oil which
8. customwas crystallized from methylene chloride-ether

ORD record

ord-b9e678ea41a84d989f5f2f0748458c06

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05324747