Acetone → HCID 66590461, compound

HRID 2363614Notes

Reaction equation

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

Participants

Reactant 3

HCID 180Acetone

HCID 12417Pivalaldehyde

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

Product 1

HCID 66590461HCID 66590461, compound

Procedure

The title compound was prepared by substituting N1-((3aR,4S,6aS)-2-{[3-(trifluoromethyl)phenyl]sulfonyl}octahydrocyclopenta[c]pyrrol-4-yl)-L-leucinamide from Step B 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 (400 MHz, pyridine-d5) δ ppm 8.38 (s, 1H), 8.30-8.33 (m, 1H), 8.20 (d, J=7.9 Hz, 1H), 7.90-7.93 (m, 1H), 7.72 (t, J=7.8 Hz, 1H), 4.20-4.26 (m, 1H), 3.86 (dd, J=9.9, 2.3 Hz, 1H), 3.35 (dd, J=8.9, 5.1 Hz, 1H), 3.14-3.20 (m, 2H), 2.97 (dd, J=9.6, 6.8 Hz, 1H), 2.83 (hept, J=6.2 Hz, 1H), 2.52-2.56 (m, 2H), 2.07-2.81 (m, 1H), 1.78-2.01 (m, 3H), 1.64 (ddd, J=13.6, 8.4, 5.2 Hz, 1H), 1.47-1.59 (m, 2H), 1.25-1.36 (m, 1H), 1.04 (d, J=6.3 Hz, 3H), 1.02 (d, J=6.1 Hz, 3H), 0.91 (d, J=6.7 Hz, 3H), 0.85 (d, J=6.6 Hz, 3H); MS (ESI−) m/z 488 (M−H)−.

Sources & evidence

ORD record: ord-689a88f389284bea9cc5570336be392f
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691865B2

Reaction notes

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