L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → Tert-butyl(s)-4,4-dimethyl-1-oxo-1-((3ar,4s,6as)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-ylamino)pentan-2-ylcarbamate

HRID 2363580Notes

Reaction equation

HRID 2363580 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:17][C:18]([F:35])([F:34])[C:19]1[N:24]=[C:23]([N:25]2[CH2:29][C@@H:28]3[C@@H:30]([NH2:33])[CH2:31][CH2:32][C@@H:27]3[CH2:26]2)[CH:22]=[CH:21][CH:20]=1.[CH2:36](N1C[C@@H]2[C@@H](N)CC[C@@H]2C1)C1C=CC=CC=1>>[CH3:36][C:11]([CH3:12])([CH3:13])[CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:14](=[O:16])[NH:33][C@@H:30]1[C@@H:28]2[C@@H:27]([CH2:26][N:25]([C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([C:18]([F:17])([F:34])[F:35])[N:24]=3)[CH2:29]2)[CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 66590059(3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 91336193Tert-butyl(s)-4,4-dimethyl-1-oxo-1-((3ar,4s,6as)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-ylamino)pentan-2-ylcarbamate

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-L-neopentylglycine for N-(tert-butoxycarbonyl)-L-leucine and (3aR,4S,6aS)-2-(6-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine from Step A 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 7.78 (s, 1H), 7.45 (s, 1H), 7.05 (s, 1H), 6.91 (d, J=7.3, 1H), 6.47 (d, J=8.6, 1H), 4.53 (td, J=8.3, 4.7, 1H), 4.28-4.19 (m, 1H), 3.67-3.56 (m, 2H), 3.52 (dd, J=10.9, 7.9, 1H), 3.27 (dd, J=11.0, 3.7, 1H), 2.76-2.66 (m, 2H), 2.13 (dd, J=14.3, 4.6, 1H), 2.06 (dt, J=12.8, 6.4, 1H), 1.91 (td, J=13.3, 7.9, 1H), 1.73 (dd, J=14.3, 8.0, 1H), 1.62 (dq, J=15.1, 7.7, 1H), 1.50 (s, 9H), 1.37 (qd, J=7.9, 4.9, 1H), 1.00 (s, 9H); MS (ESI+) m/z 499 (M+H)+.

Sources & evidence

ORD record
ord-ccad6177631b41c3a4adff7863f9124d
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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