Sulfuric Acid → (+)-(4S,5R)-3,4-Dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbutyl)-4-(4-methylpentanoyl)cyclopent-2-en-1-one

96.3 mg of the dry Mg salt of (+)-cis isohumulone ((+)-VIII) was dissolved in 1 mL of methanol. 3.1 mg (0.3 eq) of MgO was added, and the reaction mixture was stirred for five minutes. 30 mg of 10% Pd/C was added to the solution, and stirring was resumed. A hydrogen atmosphere was introduced by bubbling hydrogen gas into the solution. After 45 minutes the reaction was judged to be complete by HPLC, the stirring was stopped, and the hydrogen atmosphere was removed by opening the vial. 1 equivalent of sulfuric acid was added to the reaction mixture (pH˜1), and the reaction was filtered through a 0.2 mm syringe filter. The reaction vessel and filter were washed 2 times successively with ethyl acetate. The filtrate was concentrated in vacuo, redissolved in hexanes, dried over Na2SO4, filtered via a cotton pipette, and concentrated in vacuo and dried overnight at 0.070 mbar. 58.1 mg of (+)-KDT-500 was produced. Further purification was carried out via chromatography and crystallization.

1. stirringstirring
2. customby bubbling hydrogen gas into the solution
3. waitAfter 45 minutes the reaction was judged
4. customthe hydrogen atmosphere was removed
5. filtrationthe reaction was filtered through a 0.2 mm syringe
6. filtrationfilter
7. filtrationThe reaction vessel and filter
8. washwere washed 2 times successively with ethyl acetate
9. concentrationThe filtrate was concentrated in vacuo
10. dissolutionredissolved in hexanes
11. dry with materialdried over Na2SO4
12. filtrationfiltered via a cotton pipette
13. concentrationconcentrated in vacuo
14. customdried overnight at 0.070 mbar

ORD-Eintrag

ord-74aa34edd76f4735b8f1b1466809736f

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08829056B2