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

HRID 2363579Notes

Reaction equation

HRID 2363579 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])C.[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.C(N1C[C@@H]2[C@@H](N)CC[C@@H]2C1)C1C=CC=CC=1>>[O:16]=[C:14]([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:35])([F:34])[F:17])=[CH:24][N:23]=3)[CH2:29]2)[CH2:32][CH2:31]1)[C@@H:9]([NH:8][C:6](=[O:7])[O:5][CH:1]([CH3:3])[CH3:4])[CH2:10][CH2:11][CH3:13]

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 91465118Isopropyl(s)-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 (S)-2-(isopropoxycarbonylamino)pentanoic acid from Step A for N-(tert-butoxycarbonyl)-L-leucine and (3aR,4S,6aS)-2-(5-(trifluoromethyl)pyridin-2-yl)octahydrocyclopenta[c]pyrrol-4-amine from Step B of Example 262 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 (d, J=1.0, 1H), 7.94 (dd, J=4.3, 2.4, 1H), 7.60 (dd, J=8.9, 2.5, 1H), 7.07 (d, J=7.0, 1H), 6.35 (d, J=8.9, 1H), 5.03 (dt, J=12.5, 6.2, 1H), 4.49 (dd, J=13.9, 8.0, 1H), 4.35-4.19 (m, 1H), 3.73 (dd, J=11.3, 3.6, 1H), 3.66 (dd, J=11.3, 7.6, 1H), 3.57 (dd, J=11.0, 8.0, 1H), 3.32 (dd, J=11.2, 3.9, 1H), 2.81-2.66 (m, 2H), 2.10 (dt, J=12.4, 7.0, 1H), 2.04-1.88 (m, 2H), 1.86-1.75 (m, 1H), 1.72-1.60 (m, 1H), 1.57-1.46 (m, 2H), 1.45-1.33 (m, 1H), 1.21 (d, J=6.2, 3H), 1.18 (d, J=6.2, 3H), 0.87 (t, J=7.4, 3H); MS (ESI+) m/z 457 (M+H)+.

Sources & evidence

ORD record
ord-bcbe9159b761437e9a0a030924bd610e
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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