L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → N2-neopentyl-N1-((3aR,4S,6aS)-2-{[3-(trifluoromethyl)phenyl]sulfonyl}octahydrocyclopenta[c]pyrrol-4-yl)-L-leucinamide

HRID 1092594Notes

Reaction equation

HRID 1092594 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=O)(C)(C)C.[F:17][C:18]([F:38])([F:37])[C:19]1[CH:20]=[C:21]([S:25]([N:28]2[CH2:32][C@@H:31]3[C@@H:33]([NH2:36])[CH2:34][CH2:35][C@@H:30]3[CH2:29]2)(=[O:27])=[O:26])[CH:22]=[CH:23][CH:24]=1.[CH2:39](N1C[C@@H]2[C@@H](N)CC[C@@H]2C1)[C:40]1[CH:45]=CC=C[CH:41]=1>>[CH2:6]([NH:8][C@H:9]([C:14]([NH:36][C@@H:33]1[C@@H:31]2[C@@H:30]([CH2:29][N:28]([S:25]([C:21]3[CH:22]=[CH:23][CH:24]=[C:19]([C:18]([F:17])([F:37])[F:38])[CH:20]=3)(=[O:26])=[O:27])[CH2:32]2)[CH2:35][CH2:34]1)=[O:16])[CH2:10][CH:11]([CH3:12])[CH3:13])[C:40]([CH3:45])([CH3:41])[CH3:39]

Participants

4

Reactant 3

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 66590521(3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 68414618N2-neopentyl-N1-((3aR,4S,6aS)-2-{[3-(trifluoromethyl)phenyl]sulfonyl}octahydrocyclopenta[c]pyrrol-4-yl)-L-leucinamide

Procedure

The title compound was prepared by substituting (S)-4-methyl-2-(neopentylamino)pentanoic acid from Step A of Example 244 for N-(tert-butoxycarbonyl)-L-leucine and (3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine from 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 8.38 (s, 1H), 8.19-8.22 (m, 2H), 7.90-7.93 (m, 1H), 7.72 (t, J=7.8 Hz, 1H), 4.21-4.29 (m, 1H), 3.87 (dd, J=9.9, 2.6 Hz, 1H), 3.25 (dd, J=8.6, 5.6 Hz, 1H), 3.15-3.21 (m, 2H), 2.97 (dd, J=9.6, 7.0 Hz, 1H), 2.43-2.60 (m, 3H), 2.28-2.32 (m, 1H), 1.79-2.01 (m, 3H), 1.67-1.78 (m, 1H), 1.69 (ddd, J=13.6, 7.9, 5.7 Hz, 1H), 1.51-1.60 (m, 2H), 1.32 (ddt, J=9.3, 12.8, 6.4 Hz, 1H), 0.93 (d, J=6.6 Hz, 3H), 0.93 (s, 9H), 0.86 (d, J=6.5 Hz, 3H); MS (ESI+) m/z 518 (M+H)+.

Sources & evidence

ORD record
ord-ffcf1538489b4f4e816f0654af08b44d
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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