1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → HCID 91004015, compound

HRID 2363588Notes

Reaction equation

HRID 2363588 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13](O)=[O:14])=[O:7])(C)([CH3:3])[CH3:2].[F:16][C:17]([F:37])([F:36])[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.FC(F)(F)C1C=C(S(N2C[C@H]3[C@H](N)CC[C@H]3C2)(=O)=O)C=CC=1>>[O:14]=[C:13]([NH:35][C@@H:32]1[C@@H:30]2[C@@H:29]([CH2:28][N:27]([S:24]([C:21]3[CH:20]=[CH:19][C:18]([C:17]([F:16])([F:36])[F:37])=[CH:23][CH:22]=3)(=[O:25])=[O:26])[CH2:31]2)[CH2:34][CH2:33]1)[C@@H:9]([NH:8][C:6](=[O:7])[O:5][CH:1]([CH3:3])[CH3:2])[CH2:10][CH2:11][CH3:12]

Participants

4

Reactant 3

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 66590613(3aS,4R,6aR)-2-(3-(Trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66590926HCID 66590926, compound

Product 1

HCID 91004015HCID 91004015, compound

Procedure

The title compound was prepared by substituting (S)-2-(isopropoxycarbonylamino)pentanoic acid from Step A of Example 263 for (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid and (3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine from Step A of Example 256 for (3aS,4R,6aR)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 266: 1H NMR (501 MHz, pyridine-d5) δ ppm 8.08 (d, J=8.2, 2H), 7.96 (d, J=4.8, 1H), 7.82 (d, J=8.3, 2H), 7.18 (d, J=4.5, 2H), 5.01 (hept, J=6.2, 1H), 4.45 (dd, J=14.0, 7.7, 1H), 4.11 (dt, J=13.0, 6.7, 1H), 3.67 (dd, J=10.2, 3.0, 1H), 3.30 (dd, J=10.2, 7.6, 1H), 3.16-3.07 (m, 2H), 2.57 (h, J=9.3, 2H), 1.99-1.85 (m, 2H), 1.86-1.72 (m, 2H), 1.58-1.50 (m, 1H), 1.45 (ddd, J=20.8, 11.7, 7.2, 2H), 1.26 (ddd, J=13.1, 10.9, 6.6, 1H), 1.19 (d, J=6.2, 3H), 1.16 (d, J=6.2, 3H), 0.84 (t, J=7.4, 3H); MS (ESI+) m/z 520 (M+H)+.

Sources & evidence

ORD record
ord-7f74e94c72634bd6ac5920f3085ccc68
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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