Hydrogen Peroxide → (20S)-4,5-epoxy-21-hydroxy-20-methylpregnan-3-one benzoate
Reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:10][CH2:11][C@@H:12]([CH3:33])[C@@H:13]1[C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@H:27]([CH2:28][CH2:29]2)[C@:25]2([CH3:26])[C:20](=[CH:21][C:22](=[O:32])[CH2:23][CH2:24]2)[CH2:19][CH2:18]3)[CH2:15][CH2:14]1.OO.[OH-:36].[Na+]>CO.ClCCl.O>[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:36]1[C:20]23[C@:25]([CH3:26])([CH2:24][CH2:23][C:22](=[O:32])[CH:21]12)[C@@H:27]1[C@H:17]([C@H:16]2[C@:30]([CH3:31])([CH2:29][CH2:28]1)[C@@H:13]([C@H:12]([CH3:33])[CH2:11][OH:10])[CH2:14][CH2:15]2)[CH2:18][CH2:19]3Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Procedure
A solution of (20S)-21-hydroxy-20-methylpregn-4-en-3-one benzoate (8.9 g, 20.5 mmole) in methanol (80 mL) and dichloromethane (80mL) was cooled to 15° C. and treated sequentially with 30% hydrogen peroxide (5.0 mL) and sodium hydroxide (1.09 g) in water (6.7 mL). After 4 hours at room temperature, the product was isolated from the reaction mixture by the same procedure as described in Example 7 to give (20S)-4,5-epoxy-21-hydroxy-20-methylpregnan-3-one benzoate (1.6 g, 17.3%). IR 1720, 1280 cm-1 ; MS (CI) 451 (95%, M+1), 329 (100%, M+1 -PhCOOH); 1H NMR (CDCl3) δ0.76 (3H, s, C18 -Me), 1.13 (d, C22 -Me), 1.16 (s, C19 -Me), 2.98+3.04 (1H, s +s, C4 -H), 4.04 (1H, dd, 1/2C21 -CH2), 4.32 (1H, dd, 1/2C21 -CH2), 7.46 (2H, t), 7.57 (1H, t), 8.04 (1H, dd).
Workup
- customthe product was isolated from the reaction mixture by the same procedure
Sources & evidence
- ORD record
- ord-30ee470b8a8d48539f26cfb9936b62ee
- Source dataset
- uspto-grants-1993_02
- Patent number
- US05189032
Reaction notes
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