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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2363517Generated: October 31, 2026

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

https://huagongshe.com/reaction/2363517

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanesulfonyl chlorideHCID 31297—
ReactantN2-methyl-N1-{(3aS,4S,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamideHCID 66590643—
ReactantN1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamideHCID 66590662—
ProductN2-(cyclopropylsulfonyl)-N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamideHCID 66590232—

Reaction Steps

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)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08691865B2
Source datasetuspto-grants-2014_04
ORD IDord-e8cc8bbdea294778a7abc2805d14ca92
Source noteuspto-grants-2014_04