Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → (1S,5R,6R,7R)-6-[(3S)-3-hydroxy-5-phenyl-1-pentenyl]-7-[(4-phenylbenzoyl)oxy]-2-oxabicyclo[3.3.0]octane-3-one

Temperatur

45 °C

Pyridinium p-toluenesulfonate (50 mg) was added to a stirred solution of the compound [7a] (1.00 g) in methanol (50 mL) at room temperature. The mixture was stirred at 40-50° C. for 3-4 hours (TLC monitoring) and evaporated under reduced pressure. The residue was diluted with dichloromethane (75 mL). The solution was washed with saturated aqueous solution of sodium bicarbonate (25 mL) and brine(25 mL), dried over sodium sulfate, filtered and evaporated to give 0.69 g (81.0%) of oily residue. The residue was crystallized from a mixture of ethyl acetate and isopropyl ether to give compound [5a] as white crystals with mp 126-128° C. 1H NMR (CDCl3) is in agreement with the structure.

1. customevaporated under reduced pressure
2. additionThe residue was diluted with dichloromethane (75 mL)
3. washThe solution was washed with saturated aqueous solution of sodium bicarbonate (25 mL) and brine(25 mL)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. customevaporated

ORD-Eintrag

ord-90f6ca91168b45578b6d383026930c0b

Quelldatensatz

uspto-grants-2005_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06927300B2