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

HRID 1502624

반응식

HRID 1502624 반응식
[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]

참가 물질

4

반응물 2

HCID 1932902,2,2-Trifluoroethyl butanoateHCID 7074810Anecortave

생성물 1

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

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e8015d365053432ab222485bf261fde4
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09211295B2

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