1-Propanesulfonyl chloride → HCID 86676644, compound
Reaction equation
[CH:1]1([S:4]([N:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][NH:15][C@:16]34[CH2:50][CH2:49][C@@H:48]([C:51]([CH3:53])=[CH2:52])[C@@H:17]3[C@@H:18]3[C@@:31]([CH3:34])([CH2:32][CH2:33]4)[C@@:30]4([CH3:35])[C@@H:21]([C@:22]5([CH3:47])[C@@H:27]([CH2:28][CH2:29]4)[C:26]([CH3:37])([CH3:36])[C:25]([C:38]4[CH:46]=[CH:45][C:41]([C:42]([OH:44])=[O:43])=[CH:40][CH:39]=4)=[CH:24][CH2:23]5)[CH2:20][CH2:19]3)[CH2:9][CH2:8]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(S(Cl)(=O)=O)CC>>[CH3:34][C@:31]12[C@@:30]3([CH3:35])[C@@H:21]([C@:22]4([CH3:47])[C@@H:27]([CH2:28][CH2:29]3)[C:26]([CH3:36])([CH3:37])[C:25]([C:38]3[CH:39]=[CH:40][C:41]([C:42]([OH:44])=[O:43])=[CH:45][CH:46]=3)=[CH:24][CH2:23]4)[CH2:20][CH2:19][C@@H:18]1[C@H:17]1[C@H:48]([C:51]([CH3:53])=[CH2:52])[CH2:49][CH2:50][C@:16]1([NH:15][CH2:14][CH2:13][N:10]1[CH2:11][CH2:12][N:7]([S:4]([CH2:1][CH2:2][CH3:3])(=[O:6])=[O:5])[CH2:8][CH2:9]1)[CH2:33][CH2:32]2Participants
Procedure
The title compound was prepared following the method described in above for the synthesis of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(4-(cyclopropylsulfonyl)piperazin-1-yl)ethyl)amino)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid using propane-1-sulfonyl chloride as the reagent in Step 1. The product was isolated as a white solid (8 mg, 48%). LCMS: m/e 748.6 (M+H)+, 2.30 min (method 11). 1H NMR (400 MHz, Acetic) δ 7.99 (d, J=8.3 Hz, 2H), 7.26 (d, J=8.5 Hz, 2H), 5.34 (d, J=4.5 Hz, 1H), 4.81 (s, 1H), 4.70 (s, 1H), 3.59-3.26 (m, 7H), 3.23-3.11 (m, 1H), 3.09-2.95 (m, 6H), 2.93-2.80 (m, 1H), 2.27-1.02 (m, 24H), 1.73 (s, 3H), 1.24 (s, 3H), 1.10 (s, 3H), 1.07 (s, 3H), 1.05 (t, J=8.3 Hz, 3H), 0.98 (s, 3H), 0.97 (s, 3H).
Sources & evidence
- ORD record
- ord-e64691a64e974849bc0052ec310e3b1d
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846647B2
Reaction notes
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