Acetic Acid → 20-(1,3-Dioxolan-2-yl)-1alpha-acetoxy-3beta-(methoxymethyl)oxy-7alpha-(methoxycarbonyl)oxypregn-5-ene
Reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]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](O)([CH2:16][C@@H:17]([O:31][CH2:32][O:33][CH3:34])[CH2:18][C@@H:19]2[O:27][C:28](=[O:30])[CH3:29])[CH:14]=[CH:13]3)[CH2:10][CH2:9]1)[CH3:7].C(O)(=O)C.[C:40](=[O:45])([O:43]C)[O:41][CH3:42]>>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH:6]([C@@H:8]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]([CH2:16][C@@H:17]([O:31][CH2:32][O:33][CH3:34])[CH2:18][C@@H:19]2[O:27][C:28](=[O:30])[CH3:29])=[CH:14][C@H:13]3[O:45][C:40]([O:41][CH3:42])=[O:43])[CH2:10][CH2:9]1)[CH3:7]Participants
4
Conditions
- Temperature
- 100 °C
Procedure
In 10 ml of dimethyl carbonate was dissolved 350 mg of 20-(1,3-dioxolan-2-yl)-1α-acetoxy-3β-(methoxymethyl)oxypregn-6-en-5α-ol, following by addition of 0.2 ml of acetic acid. The mixture was stirred in an atmosphere of argon gas at a temperature of 100° C. for 12 hours. The reaction mixture was then worked up in the same manner as Example 132 to give 130 mg of 20-(1,3-dioxolan-2-yl)-1α-acetoxy-3β-(methoxymethyl)oxy-7α-(methoxycarbonyl)oxypregn-5-ene showing the following physical properties.
Sources & evidence
- ORD record
- ord-29f769e7eedb4f5db05a89a2a698c310
- Source dataset
- uspto-grants-1994_10
- Patent number
- US05359055
Reaction notes
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