10-Undecenoyl chloride → 20-Trimethylacetyloxy-5alpha-4-azapregn-1-ene-3-one
Reaction equation
[OH:1][CH:2]([C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([NH:12][C:13](=[O:23])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1)[CH3:3].[CH3:24][C:25]([CH3:30])([CH3:29])[C:26](Cl)=[O:27].OC([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)[C@H](N(C)C(=O)CC2)CC3)CC1)C.C(Cl)(=O)CCCCCCCCC=C>>[CH3:24][C:25]([CH3:30])([CH3:29])[C:26]([O:1][CH:2]([C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([CH2:19][CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([NH:12][C:13](=[O:23])[CH:14]=[CH:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1)[CH3:3])=[O:27]Participants
5
Procedure
Employing substantially the same procedure as described in Example 6, but substituting 20-hydroxy-5α-4-azapregn-1-ene-3-one and trimethylacetyl chloride for the 20-hydroxy-4-methyl-5α-4-azapregnan-3-one and 10-undecenoyl chloride, respectively, used therein, the title compound was obtained. MS M-1 calculated for C25H39NO3, mw=402.53; observed m/e 401.
Sources & evidence
- ORD record
- ord-1aa9c3b33f934b27894616405ad8e715
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05610162
Reaction notes
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