2-Dimethylaminopyridine → Ethyl beta-[[2-[[(3-nitrophenyl)carbonyl]amino]acetyl]amino]pyridine-3-propanoate

Participants

Reaction Steps

The same procedure used in the preparation of Example C was followed substituting an equivalent amount of DL-ethyl 3-amino-3-pyridyl propionate for ethyl beta-alanine hydrochloride. N,N'-Disuccinimidyl carbonate (14 g, 5.5 mmol) was added to 3-nitro-benzoyl glycine (10 g, 4.5 mmol) in dry dimethylformamide (30 mL) followed by dimethylaminopyridine (200 mg). After a period of 1 hour DL-ethyl 3-amino-3-(3-pyridyl) propionate dihydrochloride (13 g, 4.6 mmol) in 20% aqueous potassium carbonate (50 mL) was added in one portion. After complete reaction the product was collected by filtration (11.5 g, 80% yield). MS and 1H-NMR were consistent with the proposed structure.

Provenance & Evidence