HCID 86641991, compound → HCID 66590811, compound

HRID 1092636Notes

Reaction equation

HRID 1092636 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:9](=[O:32])[NH:10][C@@H:11]1[C@@H:18]2[C@@H:14]([CH2:15][N:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=3)(=[O:21])=[O:20])[CH2:17]2)[CH2:13][CH2:12]1)(C)(C)C.C(N1C[C@@H]2[C@@H](NC(=O)[C@@H](N(C)C(=O)OCCCC)CC(C)C)CC[C@@H]2C1)C1C=CC=CC=1>>[F:31][C:28]([F:29])([F:30])[C:24]1[CH:23]=[C:22]([S:19]([N:16]2[CH2:17][C@@H:18]3[C@@H:11]([NH:10][C:9](=[O:32])[C@H:8]([CH2:33][CH:34]([CH3:36])[CH3:35])[NH2:7])[CH2:12][CH2:13][C@@H:14]3[CH2:15]2)(=[O:21])=[O:20])[CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 86641991HCID 86641991, compoundHCID 131729486HCID 131729486, compound

Product 1

HCID 66590811HCID 66590811, compound

Procedure

N1-((3aR,4S,6aS)-2-{[3-(Trifluoromethyl)phenyl]sulfonyl}octahydrocyclopenta[c]pyrrol-4-yl)-L-leucinamide was prepared by substituting tert-butyl-((S)-4-methyl-1-oxo-1-((3aR,4S,6aS)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-ylamino)pentan-2-yl)carbamate from Step A for tent-butyl (S)-1-((3aR,4S,6aS)-2-benzyloctahydrocyclopenta[c]pyrrol-4-ylamino)-4-methyl-1-oxopentan-2-yl(methyl)carbamate in the procedure described in Example 348: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.44-8.32 (m, 2H), 8.19 (d, J=7.9, 1H), 7.91 (d, J=7.9, 1H), 7.79-7.66 (m, 1H), 4.72-4.38 (m, 3H), 4.29-4.15 (m, 1H), 3.84 (dd, J=9.9, 2.4, 1H), 3.60 (dd, J=9.3, 4.5, 1H), 3.06 (dt, J=21.7, 10.8, 1H), 2.92 (dd, J=9.6, 7.2, 1H), 2.57-2.45 (m, 2H), 1.98-1.76 (m, 4H), 1.61-1.43 (m, 2H), 1.26 (ddt, J=13.2, 9.9, 6.5, 1H), 0.90 (d, J=6.4, 3H), 0.84 (d, J=6.3, 3H); MS (ESI−) m/z 448 (M−H)−.

Sources & evidence

ORD record
ord-19223f850008420582996a31f48d4320
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

Loading…