N-(2-formyl-5,8-dioxo-5,8-dihydroquinolin-7-yl)acetamide → 7-N-acetyldemethyllavendamycin isoamyl ester

Participants

Reaction Steps

7-Acetamido-2-formylquinoline-5,8-dione (23) (prepared as described in Example 23) (244 mg, 0.1 mmol), L-tryptophan isoamyl ester (37) (prepared as described in Example 37) (239 mg, 1 mmol) and xylene (64 ml) were mixed. The mixture was stirred and slowly heated in an oil bath from room temperature to 110° C. over a one-hour period, and then from 110° C. to 140° C. over a 3-hr period. The hot reaction mixture was filtered to remove the brown impurity. The filtrate was evaporated under vacuum. The residue was treated with ethyl-acetate/hexane to give an orange solid (213 mg, 42% yield).

Provenance & Evidence