6,9-Difluoro-11-hydroxy-3,20-dioxopregna-1,4,16-trien-21-yl acetate → HCID 58187768, compound
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]2Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 37 °C
Procedure
To a solution of intermediate 2 (2.55 g, 6.06 mmol) in ethanol (100 ml), Candida antarctica Lipase (2 U/mg) (510 mg, 6.06 mmol) was added, and the reaction mixture was stirred at 37° C. overnight. The reaction mixture was filtered, washing with methanol, and the residue was purified by flash chromatography on silica gel, in gradient elution from DCM/AcOEt 90:10 to DCM/AcOEt 50:50, to afford the title compound (1.62 g, 70.6% yield).
Workup
- filtrationThe reaction mixture was filtered
- washwashing with methanol
- customthe residue was 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-981801bd0b40470b9417c77d8b20a8ff
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710037B2
Reaction notes
Loading…