N-Piperidinoethanol → HCID 117598900, compound

Participants

Reaction Steps

To a solution of (3aR,7S,10S,12R,21E,24aS)-7-tert-butyl-N-{(1R,2S)-1-[(cyclopropylsulfonyl)carbamoyl]-2-ethenylcyclopropyl}-19-hydroxy-5,8-dioxo-1,2,3,3a,5,6,7,8,11,12,20,23,24,24a-tetradecahydro-10H-9,12-methanocyclopenta[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-10-carboxamide (synthesized by the method described in Example 17 with intermediates A1, B6, C3) (40 mg) in THF (0.8 mL) under nitrogen was added 2-(piperidin-1-yl)ethanol (0.137 mL), trimethylphosphine (1.028 mL) and diisopropylazodicarboxylate (0.200 mL). After stirring for 18 hours, the mixture was diluted with ethyl acetate and water was added. The mixture was extracted with ethyl acetate (3×). The combined organics were dried over magnesium sulfate, filtered and concentrated. Purification by reverse phase HPLC (30%-100% ACN/0.015% TFA-water) yielded 13.2 mg of the desired product. HRMS (ES+) m/z 889.4523 (M+H)+.

Provenance & Evidence