L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → HCID 68416415, compound

HRID 2363571Notes

Reaction equation

HRID 2363571 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])C)=O)(C)(C)C.[F:17][C:18]([F:38])([F:37])[C:19]1[CH:24]=[CH:23][C:22]([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:21][CH:20]=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:22]3[CH:21]=[CH:20][C:19]([C:18]([F:17])([F:37])[F:38])=[CH:24][CH:23]=3)(=[O:26])=[O:27])[CH2:32]2)[CH2:35][CH2:34]1)=[O:16])[CH2:10][CH2:11][CH3:13])[C:40]([CH3:45])([CH3:41])[CH3:39]

Participants

4

Reactant 3

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 66590926HCID 66590926, compoundHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 68416415HCID 68416415, compound

Procedure

The title compound was prepared by substituting (S)-2-(neopentylamino)pentanoic acid from Step A of Example 246 for N-(tert-butoxycarbonyl)-L-leucine and (3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine from Step A of Example 256 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 8.37-8.38 (bs, 1H), 8.13-8.18 (m, 3H), 7.89-7.91 (m, 2H), 4.21-4.28 (m, 1H), 3.86 (dd, J=9.9, 2.9 Hz, 1H), 3.16-3.22 (m, 3H), 2.98 (dd, J=9.6, 7.3 Hz, 1H), 2.47-2.61 (m, 2H), 2.41 (d, J=11.2 Hz, 1H), 2.32 (d, J=11.2 Hz, 1H), 1.93-2.00 (m, 1H), 1.78-1.88 (m, 2H), 1.63-1.70 (m, 1H), 1.41-1.58 (m, 3H), 1.28-1.36 (m, 1H), 0.93 (s, 9H), 0.86 (t, J=7.3 Hz, 3H); MS (ESI+) m/z 504 (M+H)+.

Sources & evidence

ORD record
ord-633acee49c9041349cc7da2c6e98e2ac
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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