Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2363518Generated: October 31, 2026

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

https://huagongshe.com/reaction/2363518

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-(isobutylsulfonyl)-N1-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamideHCID 66590444—

Reaction Steps

The title compound was prepared by substituting 2-methylpropane-1-sulfonyl 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=9.3, 1H), 9.20 (d, J=7.4, 1H), 7.77 (s, 1H), 7.62 (d, J=7.6, 1H), 7.60-7.55 (m, 1H), 7.45 (t, J=7.7, 1H), 4.52-4.43 (m, 2H), 3.61 (d, J=13.5, 1H), 3.52 (d, J=13.6, 1H), 3.19-3.16 (m, 2H), 2.91 (dd, J=2.0, 9.0, 1H), 2.63-2.46 (m, 3H), 2.42 (dd, J=6.8, 8.9, 1H), 2.37 (dd, J=2.1, 9.0, 1H), 2.27 (dd, J=6.9, 8.8, 1H), 2.18 (td, J=5.8, 11.7, 1H), 2.01 (tt, J=6.7, 13.4, 1H), 1.96-1.85 (m, 2H), 1.73 (tdd, J=6.3, 10.3, 14.9, 2H), 1.45 (ddt, J=6.2, 9.0, 12.2, 1H), 1.08 (d, J=6.7, 3H), 1.04 (d, J=6.7, 3H), 0.81 (app t, J=7.0, 6H); MS (ESI+) m/z 518 (M+H)+.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08691865B2
Source datasetuspto-grants-2014_04
ORD IDord-fc5d06d2b34d4e4a960745d8f39e81bd
Source noteuspto-grants-2014_04