2-(Bromomethyl)-5-chlorothiophene → (1S,2R)-2-[(4-Chlorobenzenesulfonyl)-(5-chloro-thiophen-2-ylmethyl)-amino]-cyclohexanecarboxylic acid amide
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]2[C:18]([NH2:20])=[O:19])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:22][C:23]1[S:24][C:25]([Cl:28])=[CH:26][CH:27]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][C:23]2[S:24][C:25]([Cl:28])=[CH:26][CH:27]=2)[C@@H:12]2[CH2:17][CH2:16][CH2:15][CH2:14][C@@H:13]2[C:18]([NH2:20])=[O:19])(=[O:9])=[O:10])=[CH:4][CH:3]=1Komponenten
3
Versuchsvorschrift
The titled compound was prepared in 38% yield from (1S,2R)-2-(4-chlorobenzenesulfonylamino)-cyclohexanecarboxylic acid amide (75 mg, 0.237 mmol) and 2-bromomethyl-5-chloro-thiophene (83 mg, 0.498 mmol) according to the procedure described in Example 3: 1H NMR (400 Mz, CDCl3) δ 7.72 (d, 2 H, J=6.6), 7.59 (d, 2 H, J=8.9), 7.39 (br s, 1 H), 6.88 (d, 1 H, J=3.7), 6.79 (br s, 1 H), 4.69 (s, 2 H), 3.83 (dt, 1 H, Jd=12.7, J=3.7), 2.71 (m, 1 H), 2.52 (m, 1 H), 1.79–1.69 (m, 2 H), 1.61 (m, 1 H), 1.49–1.22 (m, 3 H), 1.11 (m, 1 H); MS m/e 469.1 (M+Na)+.