3-(Trifluoromethyl)benzenesulfonyl chloride → HCID 66589917, compound
Reaction equation
C([N:8]1[CH2:12][C@H:11]2[C@H:13]([NH:16][C:17](=[O:32])[C@@H:18]([N:23]([CH3:31])[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C@@H:19]([CH3:22])[CH2:20][CH3:21])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)C1C=CC=CC=1.C(N1C[C@H]2[C@H](NC(=O)[C@@H](N3CCOCC3)CC(C)C)CC[C@H]2C1)C1C=CC=CC=1.[F:62][C:63]([F:75])([F:74])[C:64]1[CH:69]=[CH:68][C:67]([S:70](Cl)(=[O:72])=[O:71])=[CH:66][CH:65]=1.FC(F)(F)C1C=C(S(Cl)(=O)=O)C=CC=1>>[CH3:31][N:23]([C@@H:18]([C@@H:19]([CH3:22])[CH2:20][CH3:21])[C:17](=[O:32])[NH:16][C@H:13]1[C@H:11]2[C@H:10]([CH2:9][N:8]([S:70]([C:67]3[CH:66]=[CH:65][C:64]([C:63]([F:62])([F:74])[F:75])=[CH:69][CH:68]=3)(=[O:72])=[O:71])[CH2:12]2)[CH2:15][CH2:14]1)[C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27]Participants
Procedure
The title compound was prepared by substituting tert-butyl(2S,3S)-1-(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylamino)-3-methyl-1-oxopentan-2-yl(methyl)carbamate from Step A of Example 334 for (S)—N-((3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl)-4-methyl-2-morpholinopentanamide and 4-(trifluoromethyl)benzene-1-sulfonyl chloride for 3-(trifluoromethyl)benzene-1-sulfonyl chloride in the procedures described in Example 319: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.66-8.72 (m, 1H), 8.05-8.13 (m, 2H), 7.88-7.91 (m, 2H), 4.69 (d, J=11.3 Hz, 1H), 4.15-4.22 (m, 1H), 3.73-3.87 (m, 1H), 3.16-3.23 (m, 1H), 3.11-3.18 (bs, 3H), 3.00 (t, J=8.3 Hz, 1H), 2.90 (t, J=8.4 Hz, 1H), 2.42-2.56 (m, 2H), 2.21-2.28 (m, 1H), 1.88-2.03 (m, 1H), 1.73-1.88 (m, 1H), 1.52-1.66 (m, 1H), 1.48 (s, 9H), 1.34-1.46 (m, 1H), 1.21-1.34 (m, 1H), 0.98-1.13 (m, 1H), 0.94 (d, J=6.3 Hz, 3H), 0.76-0.81 (m, 3H); MS (ESI+) m/z 562 (M+H)+.
Sources & evidence
- ORD record
- ord-7b13e4a90af249debdb2921ad94d3837
- Source dataset
- uspto-grants-2012_03
- Patent number
- US08129417B2
Reaction notes
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