6,9-Difluoro-11-hydroxy-3,20-dioxopregna-1,4,16-trien-21-yl acetate → HCID 58187768, compound

HRID 446830Notes

Reaction equation

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

Participants

Conditions

Temperature: 37 °C

Procedure

To a solution of intermediate 5 (2.55 g, 6.06 mmol) in ethanol (100 ml), Candida Antarctica Lipase (2 U/mg) (510 mg, 6.06 mmol) is added, and the reaction mixture is stirred at 37° C. overnight. The reaction mixture is filtered, washing with methanol, and the residue is purified by flash chromatography on silica gel, in gradient elution from DCM/AcOEt 90:10 to DCM/AcOEt 50:50, to afford 1.62 g of title compound (70.6% yield).

Workup

filtrationThe reaction mixture is filtered
washwashing with methanol
customthe residue is purified by flash chromatography on silica gel, in gradient elution from DCM/AcOEt 90:10 to DCM/AcOEt 50:50

Sources & evidence

ORD record: ord-93dd07d955cf43538112442ea517c8e6
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481517B2

Reaction notes

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