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

HRID 1502624Notes

Reaction equation

HRID 1502624 reaction equation
[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]

Participants

4

Reactant 2

HCID 1932902,2,2-Trifluoroethyl butanoateHCID 7074810Anecortave

Product 1

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

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e8015d365053432ab222485bf261fde4
Source dataset
uspto-grants-2015_12
Patent number
US09211295B2

Reaction notes

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