Sulfuric Acid → HCID 68867273, compound

Participants

Reaction Steps

Compound 02-6 (4.3 g, 11.7 mmol) was dissolved in MeOH (350 mL), conc. H2SO4 (2 mL) was added and the mixture was stirred for 8 days. The mixture was concentrated to half of the original volume. H2O was added and the pH was cautiously adjusted to 8 with conc. NH4OH. The aqueous layer was extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O (100 mL), brine (100 mL) and dried over Na2SO4. The solvent was removed in vacuo to give the crude product, which was purified by column chromatography (SiO2, EtOAc/hept=1/4+1% Et3N to 1/1). The product was obtained in only 80% purity according to HPLC and therefore subjected to automated column chromatography to give a-2 (2.1 g, 6.4 mmol, 55%) as a brown-yellow solid.

Provenance & Evidence