Hydrochloric Acid → HCID 86678433, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-tert-Butyl 1-ethyl (Z)—(S)-5-[(tert-butoxycarbonyl)amino]-2-(3-fluoropropyl)hex-2-enedioate (50.0 mg, 0.12 mmol) and lithium hydroxide (29.7 mg, 1.24 mmol) in ethanol (0.5 mL) and water (0.5 mL) was stirred at r.t. for 24 h, 30 min at 60° C. (microwave irradiation), and 14 h at 40° C. (oil bath). The mixture was cooled down to r.t. and acidified to pH 2 by addition of 2 N aqueous hydrochloric acid. The ethanol was then removed under reduced pressure and the aqueous solution extracted with ethyl acetate (3×10 mL). The combined organic layers were washed with brine, dried over sodium sulphate, and concentrated under reduced pressure. The crude product was purified by preparative HPLC (XBridge C18, 5 μm 150×19 mm, acetonitrile/water (0.1% TFA) gradient, 21 mL/min). Yield: 10.0 mg, 0.03 mmol, 25%.

Provenance & Evidence