alpha-Methylhydrocinnamic acid → HCID 46213051, compound

HRID 2363466Notes

Reaction equation

HRID 2363466 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.[CH3:17][CH:18]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:19](O)=[O:20].C1([C@H](CC)C(O)=O)C=CC=CC=1>>[CH2:1]([N:8]1[CH2:12][C@@H:11]2[C@@H:13]([NH:16][C:19](=[O:20])[CH:18]([CH3:17])[CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:14][CH2:15][C@@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 99862alpha-Methylhydrocinnamic acidHCID 785329(S)-2-Phenylbutyric acidHCID 25918977(3aS,4R,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 46213051HCID 46213051, 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-methyl-3-phenylpropanoic acid for (S)-2-phenylbutanoic acid in Step F of the procedure used to prepare Example 16: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.13 (dd, J=7.0, 21.3, 1H), 7.40 (ddd, J=7.5, 15.5, 25.3, 4H), 7.31-7.22 (m, 6H), 4.42-4.27 (m, 1H), 3.58 (dd, J=6.6, 13.1, 1H), 3.45 (dd, J=13.1, 21.0, 1H), 3.25-3.15 (m, 1H), 2.81-2.67 (m, 3H), 2.49-2.19 (m, 5H), 2.04 (ddd, J=6.0, 12.1, 24.6, 1H), 1.82-1.64 (m, 1H), 1.57-1.40 (m, 1H), 1.40-1.30 (m, 1H), 1.28 (d, J=6.4, 3H); MS (ESI+) m/z 363 (M+H)+.

Workup

  1. customto prepare Example 16

Sources & evidence

ORD record
ord-f9af37ea9c0b4392a75ef4466ac4dca5
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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