3-[6-(Azetidine-1-carbonyl)pyridin-3-yl]oxy-5-(1-ethyl-2-oxo-pyrrolidin-3-yl)oxy-N-(5-methylpyrazin-2-yl)benzamide → 3-[6-(Azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3S)-1-ethyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)benzamide

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Reaction Steps

From racemic 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-(1-ethyl-2-oxo-pyrrolidin-3-yl)oxy-N-(5-methylpyrazin-2-yl)benzamide (197 mg, 0.38 mmol) (Example 10), 3-[6-(azetidine-1-carbonyl)pyridin-3-yl]oxy-5-[(3R)-1-ethyl-2-oxo-pyrrolidin-3-yl]oxy-N-(5-methylpyrazin-2-yl)benzamide was separated from its enantiomer by chiral HPLC using a Merck 50 mm 20 μm Chiralcel OJ column eluting with methanol at a flow rate of 60 mL/min. 197 mg of racemic material was separated in 1 injection of 5 mL at 40 mg/ml in methanol to afford the product which eluted after its enantiomer to afford the product (51 mg, 26%). 1H NMR δ (300 MHz, CDCl3) 1.18 (t, 3H), 2.13-2.26 (m, 1H), 2.36 (quintet, 2H), 2.52-2.69 (m, 4H), 3.36-3.58 (m, 4H), 4.25 (t, 2H), 4.71 (t, 2H), 4.95 (t, 1H), 6.98 (s, 1H), 7.22 (s, 1H), 7.39 (d, 1H), 7.47 (s, 1H), 8.12 (d, 1H), 8.14 (s, 1H), 8.33 (s, 1H), 8.56 (s, 1H), 9.53 (s, 1H); m/z 517 (M+H)+.

Provenance & Evidence