L-Leucine, N-((1,1-dimethylethoxy)carbonyl)- → N-[(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-3-methylbutanamide

HRID 2363549Notes

Reaction equation

HRID 2363549 reaction equation
C(O[C:6]([NH:8][C@H:9]([C:14](O)=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])(C)(C)C.[CH2:17]([N:24]1C[C@H]2[C@H](N)CC[C@H]2[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:33](N1C[C@@H]2[C@@H](N)CC[C@@H]2C1)[C:34]1[CH:39]=CC=C[CH:35]=1>>[CH2:17]([N:24]1[CH2:25][C@H:10]2[C@H:9]([NH:8][C:6](=[O:7])[CH2:33][CH:34]([CH3:39])[CH3:35])[CH2:14][CH2:12][C@H:11]2[CH2:13]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 25918977(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amineHCID 66591011(3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590627N-[(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl]-3-methylbutanamide

Procedure

The title compound was prepared by substituting 3-methylbutanoic acid for N-(tert-butoxycarbonyl)-L-leucine and (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Step E of Example 16 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 8.30-8.17 (m, 1H), 7.43 (dd, J=11.2, 4.2, 2H), 7.37 (t, J=7.5, 2H), 7.27 (t, J=7.3, 1H), 4.49-4.39 (m, 1H), 3.60 (d, J=13.1, 1H), 3.45 (d, J=13.1, 1H), 2.89-2.78 (m, 1H), 2.55-2.49 (m, 2H), 2.45 (dd, J=10.4, 5.3, 1H), 2.36-2.24 (m, 3H), 2.21 (d, J=7.1, 2H), 2.17-2.08 (m, 1H), 1.90-1.79 (m, 1H), 1.62 (ddd, J=15.1, 12.3, 7.2, 1H), 1.40 (dtd, J=9.2, 8.2, 6.1, 1H), 0.95 (d, J=6.6, 6H); MS (ESI+) m/z 301 (M+H)+.

Sources & evidence

ORD record
ord-e6b4a1d3bc77476681737d821aeed049
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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