12-[(Propan-2-yl)sulfanyl]dodecanoic acid → 17-(12-(Isopropylthio)dodecanoyloxy)-4-methyl-5alpha-4-azaandrostan-3-on
Reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([N:12]([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3.[CH:23]([S:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38](O)=[O:39])([CH3:25])[CH3:24].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(CCCCCCCCCCC(O)=S)C>>[CH:23]([S:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][C:38]([O:1][CH:2]1[CH2:7][CH2:6][C@H:5]2[C@H:8]3[C@H:18]([CH2:19][CH2:20][C@:3]12[CH3:4])[C@:16]1([CH3:17])[C@H:11]([N:12]([CH3:22])[C:13](=[O:21])[CH2:14][CH2:15]1)[CH2:10][CH2:9]3)=[O:39])([CH3:25])[CH3:24]Participants
5
Reactant 4
Product 1
Procedure
Employing substantially the same procedure as described in Example 1, but substituting 17-hydroxy-4-methyl-5α-4-azaandrostan-3-one and 12-(isopropylthio)dodecanoic acid for the 20-hydroxy-4-methyl-5α-4-azapregnan-3-one and 11-ethylthioundecanoic acid, respectively, used therein, the title compound was obtained. MS M+ calculated for C34H59NO3S, mw=561.92; observed m/e 561.
Sources & evidence
- ORD record
- ord-bf37bd2f359f45a4a8175942f3c5f5c4
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05610162
Reaction notes
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