4-Methylmorpholine → HCID 44360270, compound

Participants

Reaction Steps

Suspend 3-(3-pyridyl)propionic acid (174 mg, 1.15 mmol, Walker, F. A. et al., J. Amer. Chem. Soc., 102, 5530-5538 (1980)) in methylene chloride (15 mL). Add N-methylmorpholine (0.38 mL, 3.45 mmol) and triethylamine (0.32 mL, 2.30 mmol), and cool the resulting clear, colorless solution to -18° C. Add isobutylchloroformate (0.15 mL, 1.15 mmol) and stir for 20 minutes. Subsequently add N-methylmorpholine (0.13 mL, 1.15 mmol) and H-Val-Pro-Val-CF2CF3.hydrochloride (520 mg, 1.15 mmol) and stir at -20° C. for 1 hour. Allow reaction mixture to warm to room temperature, dilute the reaction mixture with additional methylene chloride (35 mL) and successively wash with 1N HCl (3×20 mL), saturated NaHCO3 (2×20 mL), and brine (1×20 mL). Dry and concentrate the crude product. Purify the crude product by flash chromatography (75:25::acetone:EtOAc) to give the title compound as a white solid foam. (Yield: 470 mg, 74%, 3:1::LLL:LLD).

Provenance & Evidence