L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → Tert-butyl(s)-4,4-dimethyl-1-oxo-1-((3ar,4s,6as)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-ylamino)pentan-2-ylcarbamate

HRID 1092601Notes

Reaction equation

HRID 1092601 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[CH:20]=[CH:21][C:22]([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)=[N:23][CH:24]=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:22]3[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:34])[F:35])=[CH:24][N:23]=3)[CH2:29]2)[CH2:32][CH2:31]1

Participants

4

Reactant 3

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 66590965(3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 90785805Tert-butyl(s)-4,4-dimethyl-1-oxo-1-((3ar,4s,6as)-2-(5-(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-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine from Step B 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 8.52 (s, 1H), 7.81 (d, J=5.8, 1H), 7.60 (dd, J=8.9, 2.5, 1H), 7.07 (d, J=7.0, 1H), 6.35 (d, J=8.9, 1H), 4.53 (td, J=8.3, 4.7, 1H), 4.30-4.18 (m, 1H), 3.72 (dd, J=11.3, 3.5, 1H), 3.65 (dd, J=11.3, 7.6, 1H), 3.57 (dd, J=11.1, 7.8, 1H), 3.31 (dd, J=11.2, 3.9, 1H), 2.80-2.67 (m, 2H), 2.10 (ddd, J=19.9, 13.5, 5.8, 2H), 1.93 (td, J=13.1, 7.7, 1H), 1.74 (dd, J=14.3, 8.0, 1H), 1.64 (dq, J=12.9, 7.8, 1H), 1.50 (s, 9H), 1.44-1.33 (m, 1H), 1.00 (s, 9H); MS (ESI+) m/z 499 (M+H)+.

Sources & evidence

ORD record
ord-6ccd9a0d8b2648e79da2182c68062526
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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