Pivalaldehyde → HCID 71819115, compound

HRID 1092635Notes

Reaction equation

HRID 1092635 reaction equation
[CH3:1][C:2]([CH3:31])([CH3:30])[CH2:3][C@@H:4]([C:6]([NH:8][C@@H:9]1[C@@H:16]2[C@@H:12]([CH2:13][N:14]([S:17]([C:20]3[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[CH2:15]2)[CH2:11][CH2:10]1)=[O:7])[NH2:5].F[C:33](F)(F)[C:34]1C=C(S(N2C[C@H]3[C@H](N)CC[C@H]3C2)(=O)=O)C=C[CH:39]=1.C(=O)C(C)(C)C>CC(C)=O>[CH:34]([NH:5][C@H:4]([C:6]([NH:8][C@@H:9]1[C@@H:16]2[C@@H:12]([CH2:13][N:14]([S:17]([C:20]3[CH:21]=[CH:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=3)(=[O:19])=[O:18])[CH2:15]2)[CH2:11][CH2:10]1)=[O:7])[CH2:3][C:2]([CH3:31])([CH3:30])[CH3:1])([CH3:39])[CH3:33]

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 66590494HCID 66590494, compoundHCID 66590613(3aS,4R,6aR)-2-(3-(Trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine

Product 1

HCID 71819115HCID 71819115, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The title compound was prepared by substituting 4-methyl-N1-(3aR,4S,6aS)-2-{[4-(trifluoromethyl)phenyl]sulfonyl}octahydrocyclopenta[c]pyrrol-4-yl)-L-leucinamide from Example 419 for (3aS,4R,6aR)-2-(3-(trifluoromethyl)phenylsulfonyl)octahydrocyclopenta[c]pyrrol-4-amine and acetone for pivalaldehyde in the procedure described in Example 281: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.26-8.29 (m, 1H), 8.13-8.16 (m, 2H), 7.89-7.91 (m, 2H), 4.21-4.26 (m, 1H), 3.85 (dd, J=9.9, 2.3 Hz, 1H), 3.36 (dd, J=7.5, 4.1 Hz, 1H), 3.15-3.20 (m, 2H), 2.98 (dd, J=9.6, 6.7 Hz, 1H), 2.83 (hept, J=6.2 Hz, 1H), 2.51-2.62 (m, 2H), 1.91-1.97 (m, 1H), 1.79-1.88 (m, 2H), 1.63-1.81 (m, 1H), 1.51-1.59 (m, 1H), 1.47 (dd, J=14.1, 7.5 Hz, 1H), 1.31 (ddt, J=9.6, 12.8, 6.4 Hz, 1H), 1.03 (dd, J=6.2, 2.7 Hz, 6H), 0.98 (s, 9H); MS (ESI+) m/z 504 (M+H)+.

Sources & evidence

ORD record
ord-b7ff9c582bd64f81b6ad99df602060fd
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

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