2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromobenzoic acid → (S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromo-benzoylamino]-3-(3-bromo-4-chloro-phenyl)-propionic acid

HRID 1593907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1593907
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]([Br: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]([Br: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]=12

Komponenten

3

Edukt 2

HCID 160907442-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromobenzoic acidHCID 687686723-bromo-4-chloro-L-phenylalanine methyl ester hydrochloride

Produkt 1

HCID 45487002(S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromo-benzoylamino]-3-(3-bromo-4-chloro-phenyl)-propionic acid

Versuchsvorschrift

The title compound was prepared from 3-bromo-4-chloro-L-phenylalanine methyl ester hydrochloride and 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-bromobenzoic acid as in Example 1, Part C, followed by hydrolysis of the resulting methyl ester as in EXAMPLE 2, Part E. HPLC: RT=10.05 min. MS (ESI−): mass calcd. for C22H15Br2ClN4O5S2, 674.77; m/z found, 673/675 [M−H]−. 1H NMR (400 MHz, acetone-d6): 11.77 (s,1H), 8.46-8.42 (m,1H), 8.34-8.29 (m,1H), 8.19-8.13 (m,1H), 7.93-7.87 (m, 1H), 7.87-7.82 (m, 1H), 7.73-7.69 (m, 1H), 7.54-7.46 (m, 2H), 7.40-7.35 (m, 1H), 7.17-7.12 (m, 1H), 4.97-4.88 (m, 1H), 3.40-3.32 (m, 1H), 3.22-3.14 (m, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-d9afce37c67c440897b5381728f689ea
Quelldatensatz
uspto-grants-2007_11
Patentnummer
US07297816B2

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