HCID 86720235, compound → HCID 86720234, compound

HRID 537724Notes

Reaction equation

[OH:1][C@:2]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C:25](=[CH:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[C:3](=[O:11])[CH2:4][O:5][C:6]([CH2:8][CH:9]=[CH2:10])=[O:7]>C(OCC(F)(F)F)(=O)CCCCCCCCCCCCCCCCC.O1CCCC1>[C:2]([O:1][C@:2]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C:25](=[CH:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[C:3](=[O:11])[CH2:4][O:5][C:6]([CH2:8][CH:9]=[CH2:10])=[O:7])(=[O:1])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

Conditions

Temperature: 45 °C

Procedure

Crude 17α-hydroxy-21-allylcarbonyloxy-pregna-4,9(11)-diene-3,20-dione was dissolved in 15 g of trifluoroethyl octadecanoate and 150 ml of tetrahydrofuran, the resulting solution was added with 4 g of Bacillus subtilis protease and the suspension was stirred for 2 days at 45° C., adding further protease at regular time intervals to 3 g total. The protease was filtered off, the filtrate was removed under vacuum and the residue was chromatographed on a silica gel column with a dichloromethane/methanol 99:1 mixture. The less polar fraction was evaporated off to obtain a residue of 17α-octadecanoyloxy-21-allylcarbonyloxy-pregna-4,9(11)-diene-3,20-dione.

Workup

additionadding further protease at regular time intervals to 3 g total
filtrationThe protease was filtered off
customthe filtrate was removed under vacuum
customthe residue was chromatographed on a silica gel column with a dichloromethane/methanol 99:1 mixture
customThe less polar fraction was evaporated off

Sources & evidence

ORD record: ord-6e553c622e854547800b4ec5fc56caed
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08865690B2

Reaction notes

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