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

HRID 2265273

Reaktionsgleichung

Reaktionsgleichung von HRID 2265273
[N:1]1[S:5][N:4]=[C:3]2[C:6]([S:10]([NH:13][C:14]3[CH:22]=[C:21]([I:23])[CH:20]=[CH:19][C:15]=3[C:16](O)=[O:17])(=[O:12])=[O:11])=[CH:7][CH:8]=[CH:9][C:2]=12.Cl.[CH3:25][O:26][C:27](=[O:39])[C@@H:28]([NH2:38])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Br:37])[CH:31]=1>>[CH3:25][O:26][C:27](=[O:39])[C@@H:28]([NH:38][C:16](=[O:17])[C:15]1[CH:19]=[CH:20][C:21]([I:23])=[CH:22][C:14]=1[NH:13][S:10]([C:6]1[C:3]2=[N:4][S:5][N:1]=[C:2]2[CH:9]=[CH:8][CH:7]=1)(=[O:12])=[O:11])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[C:32]([Br:37])[CH:31]=1

Komponenten

3

Edukt 2

HCID 160906642-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acidHCID 687686723-bromo-4-chloro-L-phenylalanine methyl ester hydrochloride

Produkt 1

HCID 58999939(S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoylamino]-3-(3-bromo-4-chloro-phenyl)-propionic acid methyl ester

Versuchsvorschrift

2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-iodo-benzoic acid was coupled to (S)-2-amino-3-(3-bromo-4-chloro-phenyl)-propionic acid methyl ester hydrochloride as in EXAMPLE 1, Part C, to afford the title compound. HPLC: RT=10.85 min. MS (ESI+): mass calcd. for C23H17BrClIN4O5S2, 735.80; m/z found, 735/737 [M+H]+. 1H NMR (500 MHz, CDCl3): 11.31 (s, 1H), 8.36 (d, J=7.1, 1H), 8.22 (d, J=8.7, 1H), 8.08 (d, J=1.4, 1H), 7.72 (dd, J=8.8, 7.1, 1H), 7.36-7.28 (m, 3H), 6.96-6.90 (m, 2H), 6.46 (d, J=7.1, 1H), 4.93 (q, J=5.5, 1H), 3.82 (s, 3H), 3.23-3.10 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-53d7bf50b8884425a72b45d41b52e0d1
Quelldatensatz
uspto-grants-2010_12
Patentnummer
US07855292B2

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