Methanesulfonyl chloride → N2-(isobutylsulfonyl)-N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:33])([F:32])[C:8]1[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=1)[CH2:11][N:12]1[CH2:16][C@H:15]2[C@H:17]([NH:20][C:21](=[O:28])[C@H:22]([CH2:24][CH:25]([CH3:27])[CH3:26])[NH2:23])[CH2:18][CH2:19][C@H:14]2[CH2:13]1.CN[C@H:36]([C:41](N[C@@H]1[C@H]2[C@H](CN(CC3C=CC=C(C(F)(F)F)C=3)C2)CC1)=O)[CH2:37]C(C)C>>[CH2:1]([S:2]([NH:23][C@H:22]([C:21]([NH:20][C@H:17]1[C@H:15]2[C@H:14]([CH2:13][N:12]([CH2:11][C:10]3[CH:29]=[CH:30][CH:31]=[C:8]([C:7]([F:32])([F:6])[F:33])[CH:9]=3)[CH2:16]2)[CH2:19][CH2:18]1)=[O:28])[CH2:24][CH:25]([CH3:26])[CH3:27])(=[O:4])=[O:3])[CH:36]([CH3:41])[CH3:37]Participants
Reactant 3
Product 1
Procedure
The title compound was prepared by substituting 2-methylpropane-1-sulfonyl chloride for methanesulfonyl chloride and N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide from Example 170 Step B for N2-methyl-N1-{(3aS,4S,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide in the procedure described in Example 167: 1H NMR (500 MHz, pyridine-d5) δ ppm 9.34 (d, J=9.3, 1H), 9.20 (d, J=7.4, 1H), 7.77 (s, 1H), 7.62 (d, J=7.6, 1H), 7.60-7.55 (m, 1H), 7.45 (t, J=7.7, 1H), 4.52-4.43 (m, 2H), 3.61 (d, J=13.5, 1H), 3.52 (d, J=13.6, 1H), 3.19-3.16 (m, 2H), 2.91 (dd, J=2.0, 9.0, 1H), 2.63-2.46 (m, 3H), 2.42 (dd, J=6.8, 8.9, 1H), 2.37 (dd, J=2.1, 9.0, 1H), 2.27 (dd, J=6.9, 8.8, 1H), 2.18 (td, J=5.8, 11.7, 1H), 2.01 (tt, J=6.7, 13.4, 1H), 1.96-1.85 (m, 2H), 1.73 (tdd, J=6.3, 10.3, 14.9, 2H), 1.45 (ddt, J=6.2, 9.0, 12.2, 1H), 1.08 (d, J=6.7, 3H), 1.04 (d, J=6.7, 3H), 0.81 (app t, J=7.0, 6H); MS (ESI+) m/z 518 (M+H)+.
Sources & evidence
- ORD record
- ord-fc5d06d2b34d4e4a960745d8f39e81bd
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691865B2
Reaction notes
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