1,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)- → tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)hexan-2-yl)carbamate

HRID 2363586Notes

Reaction equation

HRID 2363586 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:19]=[C:20]([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:21]=[CH:22][CH:23]=1.F[C:39](F)(F)[C:40]1C=C(S(N2C[C@H]3[C@H](N)CC[C@H]3C2)(=O)=O)C=CC=1>>[CH3:12][N:8]([C@@H:9]([CH2:10][CH2:11][CH2:39][CH3:40])[C:13](=[O:15])[NH:35][C@@H:32]1[C@@H:30]2[C@@H:29]([CH2:28][N:27]([S:24]([C:20]3[CH:21]=[CH:22][CH:23]=[C:18]([C:17]([F:16])([F:36])[F:37])[CH:19]=3)(=[O:25])=[O:26])[CH2:31]2)[CH2:34][CH2:33]1)[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 66590521(3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amineHCID 66590613(3aS,4R,6aR)-2-(3-(Trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 66590151tert-butyl methyl((S)-1-oxo-1-((3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)hexan-2-yl)carbamate

Procedure

The title compound was prepared by substituting N-(tert-butoxycarbonyl)-N-methyl-L-norleucine for (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid and (3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine from Step D of Example 252 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 8.44 (d, J=6.9 Hz, 1H), 8.36-8.38 (bs, 1H), 8.19 (d, J=7.9 Hz, 1H), 7.91 (d, J=7.6 Hz, 1H), 7.72 (t, J=7.8 Hz, 1H), 5.0 (m, 0.7H), 4.6 (m, 0.3H), 4.18-4.24 (m, 1H), 3.83-3.86 (m, 1H), 3.13-3.19 (m, 1H), 3.08-3.13 (m, 1H), 2.97-3.10 (bs, 3H), 2.91 (dd, J=9.4, 7.4 Hz, 1H), 2.44-2.59 (m, 2H), 1.98-2.19 (m, 1H), 1.84-1.98 (m, 1H), 1.72-1.85 (m, 2H), 1.47-1.60 (m, 1H), 1.44-1.46 (m, 9H), 1.22-1.34 (m, 1H), 1.15-1.34 (m, 4H), 0.76-0.81 (m, 3H); MS (ESI+) m/z 562 (M+H)+, 579 (M+NH4)+.

Sources & evidence

ORD record
ord-e937b3125f8e4d139fd1e8c712774fde
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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