N-(tert-butoxycarbonyl)glycine → Tert-butyl{2-oxo-2-[(2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl)(phenyl)amino]ethyl}carbamate

Participants

Reaction Steps

To a mixture of 2-anilino-N-[4-(4-pyridinyl)phenyl]acetamide (50.0 mg) and [(tert-butoxycarbonyl)amino]acetic acid (86.6 mg) in N,N-dimethylformamide (1.0 mL) were added diisopropylethylamine (0.189 mL) and N-[(dimethylamino) (3H-[1,2,3]triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methylmethanaminium hexafluorophosphate (207 mg) at ambient temperature and the mixture was stirred at the same temperature for 24 hours. Water (3.0 mL) was added to the mixture and the resulting mixture was extracted with ethyl acetate (6.0 mL). The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by preparative thin-layer chromatography (10% methanol in chloroform) to afford tert-butyl{2-oxo-2-[(2-oxo-2-{[4-(4-pyridinyl)phenyl]amino}ethyl)(phenyl)amino]ethyl}carbamate (36.5 mg) as yellow crystals.

Provenance & Evidence