2,2,2-Trifluoroethyl butanoate → 17alpha-Hydroxy-21-butanoyloxy-pregna-4,9(11)-diene-3,20-dione

HRID 537721

Reaktionsgleichung

Reaktionsgleichung von HRID 537721
[OH:1][C@:2]1([C@:23]2([CH3:24])[C@H:9]([C@H:10]3[C:20](=[CH:21][CH2:22]2)[C@:18]2([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH2:16][CH2:17]2)[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)[C:3](=[O:6])[CH2:4][OH:5].[C:26](OCC(F)(F)F)(=[O:30])[CH2:27][CH2:28][CH3:29]>CC(C)=O>[OH:1][C@:2]1([C@:23]2([CH3:24])[C@H:9]([C@H:10]3[C:20](=[CH:21][CH2:22]2)[C@:18]2([CH3:19])[C:13](=[CH:14][C:15](=[O:25])[CH2:16][CH2:17]2)[CH2:12][CH2:11]3)[CH2:8][CH2:7]1)[C:3](=[O:6])[CH2:4][O:5][C:26](=[O:30])[CH2:27][CH2:28][CH3:29]

Komponenten

4

Edukt 2

HCID 1932902,2,2-Trifluoroethyl butanoateHCID 7074810Anecortave

Produkt 1

HCID 8672023217alpha-Hydroxy-21-butanoyloxy-pregna-4,9(11)-diene-3,20-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

A mixture of 1 g (2.879 mM) of 17α,21-dihydroxy-pregna-4,9(11)-diene-3,20-dione and 10 ml of trifluoroethyl butanoate in 100 ml of acetone was reacted at 45° C. in the presence of 5 g of Candida cylindracea lipase for 8-10 hours, adding 1 g of lipase at regular time intervals. After completion of the reaction, the lipase was filtered off and the filtrate was concentrated under vacuum, taking up the residue three times with acetone. The semi-solid residue was purified by chromatography on a silica gel column with a dichloromethane/methanol 99:1 mixture. The less polar components were removed, to obtain the richer fraction which was evaporated to yield 0.95 g (2.29 mM) of 17α-hydroxy-21-butanoyloxy-pregna-4,9(11)-diene-3,20-dione.

Aufarbeitung

  1. customwas reacted at 45° C. in the presence of 5 g of Candida cylindracea lipase for 8-10 hours
  2. additionadding 1 g of lipase at regular time intervals
  3. customAfter completion of the reaction
  4. filtrationthe lipase was filtered off
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe semi-solid residue was purified by chromatography on a silica gel column with a dichloromethane/methanol 99:1 mixture
  7. customThe less polar components were removed
  8. customto obtain the richer fraction which
  9. customwas evaporated

Quellen und Nachweise

ORD-Eintrag
ord-b02d7551d0684fd2b2feceb34728a024
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865690B2

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