2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acid → (S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3-bromo-4-chloro-phenyl)-propionic acid
Reaktionsgleichung
Cl.C[O:3][C:4](=[O:16])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Br:15])[CH:9]=1)[NH2:6].[N:17]1[S:21][N:20]=[C:19]2[C:22]([S:26]([NH:29][C:30]3[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:31]=3[C:32](O)=[O:33])(=[O:28])=[O:27])=[CH:23][CH:24]=[CH:25][C:18]=12>>[N:17]1[S:21][N:20]=[C:19]2[C:22]([S:26]([NH:29][C:30]3[CH:38]=[C:37]([Cl:39])[CH:36]=[CH:35][C:31]=3[C:32]([NH:6][C@@H:5]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Br:15])[CH:9]=3)[C:4]([OH:3])=[O:16])=[O:33])(=[O:28])=[O:27])=[CH:23][CH:24]=[CH:25][C:18]=12Komponenten
Versuchsvorschrift
(S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3-bromo-4-chloro-phenyl)-propionic acid was prepared from 3-bromo-4-chloro-L-phenylalanine methyl ester hydrochloride and 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoic acid as in EXAMPLE 1, Part C. Hydrolysis of the methyl ester as in EXAMPLE 2, Part E, provided the title compound. HPLC: RT=10.07 min. MS (ESI−): mass calcd. for C22H15BrCl2N4O5S2, 630.32; m/z found, 629/631 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.35 (s, 1H), 8.36 (d, J=7.0, 1H), 8.20 (d, J=8.8, 1H), 7.76-7.69 (m, 2H), 7.41 (d, J=1.7, 1H), 7.36 (d, J=8.2, 1H), 7.17 (d, J=8.5, 1H), 7.05 (dd, J=8.2, 1.8, 1H), 6.91 (dd, J=8.4, 1.8, 1H), 6.53 (d, J=7.1, 1H), 5.04-4.95 (m, 1H), 3.36-3.15 (m, 2H).
Quellen und Nachweise
- ORD-Eintrag
- ord-b249f92565a7499a93664f304dd6be20
- Quelldatensatz
- uspto-grants-2010_12
- Patentnummer
- US07855292B2
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