Triethylamine → HCID 70489191, compound

Participants

Reaction Steps

A solution of hydroxy-acid 14 (0.64 g, 3.1 mmol) and dry triethylamine (2.42 g, 24 mmol) in dry acetonitrile (200 mL) was added over 20 hr via a fixed-rate addition funnel and a high dilution head to a refluxing solution of 2-chloro-N-methyl-pyridinium iodide (3.18 g, 12.4 mmol) in dry acetonitrile (200 mL), under argon. The resulting solution was refluxed a further 2 hr, cooled, and concentrated in vacuo. The residue was taken up in pentane (50 mL) and washed with water (50 mL). The aqueous phase was extracted twice more with pentane (25 mL), and the combined pentane extracts were washed with water and brine, dried (MgSO4) and concentrated in vacuo. The residue was flash chromatographed (hexane:EtOAc, 40:1), yielding 45 mg (7.5% yield) of macrolide II. ##STR3##

Provenance & Evidence