Methanesulfonyl chloride → N2-(cyclopropylsulfonyl)-N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

HRID 2363517Notes

Reaction equation

HRID 2363517 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:33])([F:32])[C:8]1[CH:9]=[C:10]([CH:29]=[CH:30][CH:31]=1)[CH2:11][N:12]1[CH2:16][C@H:15]2[C@H:17]([NH:20][C:21](=[O:28])[C@H:22]([CH2:24][CH:25]([CH3:27])[CH3:26])[NH2:23])[CH2:18][CH2:19][C@H:14]2[CH2:13]1.CN[C@H:36](C(N[C@@H]1[C@H]2[C@H](CN(CC3C=CC=C(C(F)(F)F)C=3)C2)CC1)=O)[CH2:37]C(C)C>>[CH:1]1([S:2]([NH:23][C@H:22]([C:21]([NH:20][C@H:17]2[C@H:15]3[C@H:14]([CH2:13][N:12]([CH2:11][C:10]4[CH:29]=[CH:30][CH:31]=[C:8]([C:7]([F:32])([F:6])[F:33])[CH:9]=4)[CH2:16]3)[CH2:19][CH2:18]2)=[O:28])[CH2:24][CH:25]([CH3:26])[CH3:27])(=[O:4])=[O:3])[CH2:37][CH2:36]1

Participants

4

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 66590643N2-methyl-N1-{(3aS,4S,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamideHCID 66590662N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

Product 1

HCID 66590232N2-(cyclopropylsulfonyl)-N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide

Procedure

The title compound was prepared by substituting cyclopropanesulfonyl chloride for methanesulfonyl chloride and N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide from Example 170 Step B for N2-methyl-N1-{(3aS,4S,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide in the procedure described in Example 167: 1H NMR (500 MHz, pyridine-d5) δ ppm 9.34 (d, J=9.4, 1H), 9.03 (d, J=7.2, 1H), 7.76 (s, 1H), 7.60 (d, J=10.5, 2H), 7.44 (dd, J=6.1, 13.8, 1H), 4.45 (dd, J=6.4, 11.7, 2H), 3.57 (d, J=13.5, 1H), 3.49 (d, J=13.5, 1H), 2.84 (dd, J=2.4, 9.1, 1H), 2.80-2.73 (m, 1H), 2.61-2.50 (m, 2H), 2.38 (dd, J=7.0, 8.9, 1H), 2.34 (dd, J=2.5, 9.0, 1H), 2.28-2.23 (m, 1H), 2.18 (td, J=5.8, 11.9, 1H), 2.04 (dt, J=6.9, 20.3, 1H), 1.91 (ddd, J=4.1, 7.2, 14.3, 2H), 1.77 (ddd, J=5.3, 8.7, 13.8, 1H), 1.73-1.65 (m, 1H), 1.44 (ddd, J=6.1, 12.3, 18.6, 1H), 1.33 (td, J=4.7, 11.0, 1H), 1.22-1.16 (m, 1H), 0.91 (ddd, J=4.5, 8.5, 11.2, 1H), 0.88-0.85 (m, 1H), 0.84 (d, J=6.7, 3H), 0.82 (d, J=6.6, 3H); MS (ESI+) m/z 502 (M+H)+.

Sources & evidence

ORD record
ord-e8cc8bbdea294778a7abc2805d14ca92
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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