L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → HCID 66590478, compound

HRID 2363575Notes

Reaction equation

HRID 2363575 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]1[CH:23]=[CH:22][C:21]([S:24]([N:27]2[CH2:31][C@@H:30]3[C@@H:32]([NH2:35])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)(=[O:26])=[O:25])=[CH:20][CH:19]=1.[CH2:36](N1C[C@@H]2[C@@H](N)CC[C@@H]2C1)[C:37]1[CH:42]=CC=C[CH:38]=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([S:24]([N:27]2[CH2:31][C@@H:30]3[C@@H:32]([NH:35][C:14](=[O:16])[C@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[NH:8][CH2:6][C:37]([CH3:42])([CH3:38])[CH3:36])[CH2:33][CH2:34][C@@H:29]3[CH2:28]2)(=[O:25])=[O:26])=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 66590552HCID 66590552, compoundHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590478HCID 66590478, compound

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-(4-fluorophenylsulfonyl)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 (500 MHz, pyridine-d5) δ ppm 8.21-8.23 (m, 1H), 7.99-8.02 (m, 2H), 7.32 (t, J=8.5 Hz, 2H), 4.23-4.29 (m, 1H), 3.78 (dd, J=9.9, 2.9 Hz, 1H), 3.26 (dd, J=8.5, 5.7 Hz, 1H), 3.12-3.18 (m, 2H), 2.96 (dd, J=9.6, 7.1 Hz, 1H), 2.51-2.60 (m, 2H), 2.44-2.47 (m, 1H), 2.29-2.32 (m, 1H), 1.93-2.01 (m, 1H), 1.81-1.93 (m, 2H), 1.67-1.79 (m, 1H), 1.70 (ddd, J=13.5, 7.8, 5.7 Hz, 1H), 1.53-1.60 (m, 2H), 1.23-1.36 (m, 1H), 0.93 (d, J=6.7 Hz, 3H), 0.93 (s, 9H), 0.87 (d, J=6.5 Hz, 3H); MS (ESI+) m/z 468 (M+H)+.

Sources & evidence

ORD record
ord-872e994954364e3cbdefcebd54814623
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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