Methanol → Osaterone

HRID 2072896Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 116 mg of 17α-acetoxy-6-chloro-2-oxapregna-4,6-diene-3,20-dione, 0.5 ml of an about 28% methanol solution of sodium methylate, 0.1 ml of tetrahydrofuran and 5 ml of methanol was heated at 70° C. for 10 minutes. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with a 30% aqueous solution of hydrogen chloride and then with a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the crude product was purified by TLC [developing solvent: chloroform/acetone (19/1)] to give 70 mg of 6-chloro-17α-hydroxy-2-oxapregna-4,6-diene-3,20-dione.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with a 30% aqueous solution of hydrogen chloride
dry with materialwith a saturated aqueous solution of sodium hydrogen carbonate, and dried over anhydrous magnesium sulfate
customThe solvent was evaporated
customthe crude product was purified by TLC [developing solvent: chloroform/acetone (19/1)]

Sources & evidence

ORD record: ord-9b55a5f783be4dc4ad555ade5addc587
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04914106

Reaction notes

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