Sodium Iodide → Methyl 2-[(2-methoxy-2-oxoethyl)amino]acetate

A mixture of 10.0 g (0.022 mol) of 5-amino-N,N'-didecyl-1,3-benzenedicarboxamide, 31 ml (0.33 mol) of methyl bromoacetate, 6.6 g (0.044 mol) of sodium iodide, 6.1 g (0.044 mol) of potassium carbonate and 0.32 g (0.001 mol) of tetrabutylammonium bromide in 100 ml of DMF was stirred and heated at 100° for 67 hours. The reaction mixture was concentrated on the oil pump and 100 ml of saturated NaHCO3 solution was added to the residue. The product was extracted with ethyl acetate and the extract was washed with 10% sodium bisulfite solution. The dried extract was concentrated at reduced pressure to an oil which was purified by HPLC using 35% ethyl acetate-toluene. The combined pure fractions were crystallized from methanol-water to give 8.2 g (63% yield, mp 71°-75°) of N-[3,5-bis[decylamino)carbonyl]phenyl]-N-(2-methoxy-2-oxoethyl)glycine methyl ester.

1. temperatureheated at 100° for 67 hours
2. concentrationThe reaction mixture was concentrated on the oil pump and 100 ml of saturated NaHCO3 solution
3. additionwas added to the residue
4. extractionThe product was extracted with ethyl acetate
5. washthe extract was washed with 10% sodium bisulfite solution
6. extractionThe dried extract
7. concentrationwas concentrated at reduced pressure to an oil which
8. customwas purified by HPLC
9. customThe combined pure fractions were crystallized from methanol-water

ORD record

ord-9cdd9106293840598f5b4602ae9edcd7

Source dataset

uspto-grants-1994_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05324747