1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)pentan-2-yl)carbamate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:16][C:17]([F:37])([F:36])[C:18]1[CH:19]=[C:20]([S:24]([N:27]2[CH2:31][C@@H:30]3[C@@H:32]([NH2:35])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)(=[O:26])=[O:25])[CH:21]=[CH:22][CH:23]=1.F[C:39](F)(F)C1C=C(S(N2C[C@H]3[C@H](N)CC[C@H]3C2)(=O)=O)C=CC=1>>[CH3:12][N:8]([C@@H:9]([CH2:10][CH2:11][CH3:39])[C:13](=[O:15])[NH:35][C@@H:32]1[C@@H:30]2[C@@H:29]([CH2:28][N:27]([S:24]([C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:36])[F:37])[CH:19]=3)(=[O:25])=[O:26])[CH2:31]2)[CH2:34][CH2:33]1)[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 3
Product 1
Procedure
The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-norvaline for (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid and (3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine from Step D of Example 252 for (3aS,4R,6aR)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 266: 1H NMR (500 MHz, pyridine-d5, temperature 90° C.) δ ppm 8.30-8.31 (bs, 1H), 8.14 (d, J=7.9 Hz, 1H), 7.84 (d, J=7.8 Hz, 1H), 7.64 (t, J=7.8 Hz, 1H), 7.49 (d, J=5.6 Hz, 1H), 4.72-4.73 (m, 1H), 4.04-4.11 (m, 1H), 3.67 (dd, J=10.1, 3.3 Hz, 1H), 3.26 (dd, J=10.1, 7.7 Hz, 1H), 3.10-3.13 (m, 2H), 2.93 (s, 3H), 2.46-2.59 (m, 2H), 1.86-2.01 (m, 2H), 1.71-1.84 (m, 2H), 1.46-1.58 (m, 1H), 1.45 (s, 9H), 1.29-1.36 (m, 2H), 1.22-1.30 (m, 1H), 0.86 (t, J=7.3 Hz, 3H); MS (ESI+) m/z 548 (M+H)+.
Sources & evidence
- ORD record
- ord-7e27c8fb5e28412abbfc54e1903ee74b
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691865B2
Reaction notes
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