1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → HCID 66591209, compound

HRID 2363606Notes

Reaction equation

HRID 2363606 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([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)[C:40]1[CH:41]=[C:42](S(N2C[C@H]3[C@H](N)CC[C@H]3C2)(=O)=O)C=[CH:44][CH:45]=1>>[CH:11]1([CH2:10][C@H:9]([N:8]([CH3:12])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[C:13](=[O:15])[NH:35][C@@H:32]2[C@@H:30]3[C@@H:29]([CH2:28][N:27]([S:24]([C:21]4[CH:20]=[CH:19][C:18]([C:17]([F:16])([F:36])[F:37])=[CH:23][CH:22]=4)(=[O:25])=[O:26])[CH2:31]3)[CH2:34][CH2:33]2)[CH2:42][CH2:41][CH2:40][CH2:45][CH2:44]1

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 66591209HCID 66591209, compound

Procedure

tert-Butyl(S)-3-cyclohexyl-1-oxo-1-((3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)propan-2-yl(methyl)carbamate was prepared by substituting (S)-2-(tert-butoxycarbonyl(methyl)amino)-3-cyclohexylpropanoic acid for (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid and (3aR,4S,6aS)-2-(4-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine from Example 256 Step A for (3aS,4R,6aR)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine in the procedure described in Example 266: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.51 (d, J=6.9, 1H), 8.13 (d, J=8.2, 2H), 7.90 (d, J=8.3, 2H), 5.23-5.14 (m, 0.4H), 4.89-4.79 (m, 0.6H), 4.28-4.15 (m, 1H), 3.83 (d, J=10.6, 1H), 3.17-3.01 (m, 5H), 2.94 (dd, J=9.4, 7.2, 1H), 2.57-2.48 (m, 2H), 1.99-1.74 (m, 5H), 1.67 (d, J=13.1, 1H), 1.62-1.48 (m, 4H), 1.45 (s, 9H), 1.34-1.20 (m, 2H), 1.18-1.00 (m, 3H), 0.98-0.85 (m, 1H), 0.81-0.66 (m, 1H); MS (ESI+) m/z 602 (M+H)+.

Sources & evidence

ORD record
ord-14af20ffa2694d11a04b846ef5d7f2d3
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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