4-Methylmorpholine → HCID 131719740, compound

Participants

Reaction Steps

To the benzodiazepin-2-one 29 (0.55 g, 1.23 mmol), in tetrahydrofuran (4 mL) at -20° C. under argon, was added NMM (0.14 mL, 1.23 mmol) followed by isobutylchloroformate (9.16 mL, 1.23 mmol). The mixture was stirred for 5 minutes, and then 0.14 mL (1.23 mmol) of NMM was added, followed by isoleucine methyl ester (0.22 g, 1.23 mmol) in tetrahydrafuran. This solution was stirred for 1 hour at -20° C., then 2 hours at room temperature. Tetrahydrafuran was removed in vacuum and the resulting solid was dissolved in ethylacetate, and the salts filtered off. The ethyl acetate extract was washed with 5% citric acid, 5% sodium bicarbonate solution, water, brine and dried over MgSO4. Solvent evaporated to give 0.70 g of the crude 2-isoleucyl diazepine 30. This was chromatographed on silica gel column using 40% ethyl acetate/60% hexane to give 0.59 g of pure 30 (92% yield).

Provenance & Evidence