2,2,2-Trifluoroethyl butanoate → 17alpha-Hydroxy-21-butanoyloxy-pregna-4-ene-3,20-dione

HRID 537722Notes

Reaction equation

HRID 537722 reaction equation
[OH:1][C@:2]1([C@:23]2([CH3:24])[C@H:9]([C@H:10]3[C@H:20]([CH2:21][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]>C(C(C)=O)C>[OH:1][C@:2]1([C@:23]2([CH3:24])[C@H:9]([C@H:10]3[C@H:20]([CH2:21][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 44070711-Deoxycortisol

Product 1

HCID 8672023317alpha-Hydroxy-21-butanoyloxy-pregna-4-ene-3,20-dione

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 1 g of 17α,21-dihydroxy-pregna-4-ene-3,20-dione and 10 ml of trifluoroethyl butanoate in 50 ml of methyl ethyl ketone was reacted at 45° C. in the presence of 5 g of Candida cylindracea lipase for 8-10 hours, adding at regular time intervals 1 g of lipase. After completion of the reaction, the lipase was filtered off, the filtrate was concentrated under vacuum, taking up the residue three times with solvent. The semi-solid residue was purified by chromatography on a silica gel column with a dichloromethane/methanol 99:1 mixture. The richer fraction was evaporated to obtain 0.89 g (2.14 mM) of 17α-hydroxy-21-butanoyloxy-pregna-4-ene-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 at regular time intervals 1 g of lipase
  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 richer fraction was evaporated

Sources & evidence

ORD record
ord-d04c95c59edb4525aac4e0f9cbbe706a
Source dataset
uspto-grants-2014_10
Patent number
US08865690B2

Reaction notes

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