Glycine, N-(3-nitrobenzoyl)- → N-[2-[[(3-nitrophenyl)carbonyl]amino]-1-oxoethyl]-beta-alanine, ethyl ester

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Reaction Steps

N,N'-Disuccinimidyl carbonate (14 g, 5.5 mmol) was added to 3-nitrobenzoyl glycine (10 g, 4.5 mmol) of Example BB in dry dimethylformamide (30 mL) followed by N,N-dimethylaminopyridine (200 mg). After a period of 1 hour beta-alanine ethyl ester hydrochloride (7 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 (14 g, 97% yield). 1H-NMR (d6 -DMSO) δ, 1.18 (t, 3H, J=7.2 Hz), 2.46 (t, 2H, J=7.0), 3.34 (q, 2H, J1 =6.7 Hz, J2 =12.6 Hz), 3.87 (d, 2H, J=5.9 Hz), 4.05 (q, 2H, J1 =7.4 Hz, J2 =14.2 Hz), 7.8 (t, 1H, J=8.0 Hz), 8.1 (t, 1H, J=5.6 Hz), 8.35 (m, 2H), 8.71 (s, 1H), 9.22 (bs, 1H).

Provenance & Evidence