2-Benzyl-3,3-dimethylbutanoic acid → HCID 46213050, compound

HRID 2363464Notes

Reaction equation

HRID 2363464 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@H:13]([NH2:16])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:17]([CH:24]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:25](O)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1([C@H](CC)C(O)=O)C=CC=CC=1>>[CH2:17]([CH:24]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:25]([NH:16][C@@H:13]1[C@@H:11]2[C@@H:10]([CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:12]2)[CH2:15][CH2:14]1)=[O:26])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 1842542-Benzyl-3,3-dimethylbutanoic acidHCID 785329(S)-2-Phenylbutyric acidHCID 25918977(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 46213050HCID 46213050, compound

Procedure

The title compound was prepared by substituting (3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine from Step A of Example 33 for (3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine and 2-benzyl-3,3-dimethylbutanoic acid for (S)-2-phenylbutanoic acid in Step F of the procedure used to prepare Example 16: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.08 (dd, J=7.4, 13.6, 1H), 7.46 (d, J=7.3, 1H), 7.44-7.40 (m, 1H), 7.38 (dd, J=7.6, 15.7, 2H), 7.34 (d, J=4.3, 2H), 7.31-7.23 (m, 4H), 4.36-4.29 (m, 1H), 3.59 (d, J=13.1, 0.5H), 3.53 (dd, J=13.2, 32.6, 1H), 3.40 (d, J=13.1, 0.5H), 3.25 (q, J=12.0, 1H), 2.79-2.67 (m, 2H), 2.48-2.42 (m, J=7.0, 1H), 2.41-2.23 (m, 3.5H), 2.20 (t, J=8.3, 0.5H), 2.12 (d, J=6.7, 0.5H), 2.06 (dd, J=5.9, 11.7, 0.5H), 1.88 (dd, J=5.8, 11.7, 0.5H), 1.74 (dd, J=9.4, 16.4, 0.5H), 1.60 (dd, J=7.0, 13.2, 0.5H), 1.51-1.42 (m, 0.5H), 1.37-1.21 (m, 2H), 1.15 (s, 9H); MS (ESI+) m/z 405 (M+H)+.

Workup

  1. customto prepare Example 16

Sources & evidence

ORD record
ord-717a1f88568444e8aba8d167b46d9aa4
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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