4-Methylmorpholine → Ethyl-3-[[4-[[4-(aminoiminomethyl)phenyl]amino]-1,4-dioxobutyl]amino]-butanoate

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Reaction Steps

4-[[4-(aminoiminomethyl)phenyl]-amino]-4-oxobutanoic acid hydrochloride prepared in Example 1, Step 1 (5 g, 18 mmol) was added to dry DMF (100 ml) followed by N-methylmorpholine (2.2 g, 22 mmol) and isobutyl chloroformate (2.8 g, 22 mmol) at 25° C. The mixture was stirred for 5 min. Ethyl 3-amino butyrate (2.5 g, 22 mmol) was added followed by dimethylaminopyridine. After 1 hr, the solvent was removed under reduced pressure and the product was purified by reverse phase chromatography (0.05% TPA water/acetonitrile) to give 4.4 g of white solid: 1H NMR (d6 -DMSO) δ 1.06 (d, 3H, J=7 Hz), 2.3-2.6 (m, 6H), 4.05 (m, 3H), 7.8 (s, 4H), 7.9 (d, 1H, J=8 Hz), 9.1 (bs, 2H), 9.2 (bs, 2H), 10.4 (s, 1H); MS (FAB) m/z 349.2 (MH+), 321, 218.

Provenance & Evidence