L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → tert-Butyl((S)-1-oxo-1-((3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylamino)pentan-2-yl)carbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:17]([C@H:20]1[C@H:27]2[C@H:23]([CH2:24][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:26]2)[CH2:22][CH2:21]1)=[N+]=[N-].C(N1C[C@@H]2[C@@H](N)CC[C@@H]2C1)C1C=CC=CC=1>>[C:1]([O:5][C:6](=[O:7])[NH:8][C@@H:9]([CH2:10][CH2:11][CH3:13])[C:14](=[O:16])[NH:17][C@H:20]1[C@H:27]2[C@H:23]([CH2:24][N:25]([CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH2:26]2)[CH2:22][CH2:21]1)([CH3:2])([CH3:3])[CH3:4]Participants
Reactant 3
Product 1
Procedure
tert-Butyl((S)-1-oxo-1-((3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylamino)pentan-2-yl)carbamate was prepared by substituting N-(tert-butoxycarbonyl)-L-norvaline for N-(tert-butoxycarbonyl)-L-leucine and (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Example 16 Step D for (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 221: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.58 (d, J=7.2, 1H), 7.91 (d, J=8.3, 1H), 7.42 (d, J=7.3, 2H), 7.36 (t, J=7.4, 2H), 7.27 (t, J=7.2, 1H), 4.64 (dd, J=14.4, 7.7, 1H), 4.45-4.34 (m, 1H), 3.56 (d, J=13.1, 1H), 3.40 (d, J=13.2, 1H), 2.74 (d, J=8.9, 1H), 2.48 (d, J=0.7, 2H), 2.39-2.27 (m, 2H), 2.26-2.19 (m, 1H), 2.14 (dq, J=12.0, 6.0, 1H), 2.07-1.96 (m, 1H), 1.85 (td, J=13.8, 8.2, 2H), 1.65 (td, J=14.3, 7.3, 1H), 1.49 (d, J=8.5, 11H), 1.45-1.33 (m, 1H), 0.81 (t, J=7.3, 3H); MS (ESI+) m/z 416 (M+H)+.
Sources & evidence
- ORD record
- ord-1a5e01cd7e26458a99e29e05525d96e8
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691865B2
Reaction notes
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