Hydrochloric Acid → (E)-(S)-5-Amino-2-(3-fluoropropyl)hex-2-enedioic acid

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Reaction Steps

A mixture of 6-tert-Butyl 1-ethyl (E)-(S)-5-[(tert-butoxycarbonyl)amino]-2-(3-fluoropropyl)hex-2-enedioate (1e) (80.0 mg, 0.20 mmol) and 4 N aqueous hydrochloric acid (1 mL) was heated to reflux for 4 h. The mixture was then cooled to r.t., diluted with water (5 mL) and lyophilised. 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: 12.0 mg, 0.04 mmol, 19%.

Provenance & Evidence