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-fluoro-phenyl)-propionic acid

HRID 1593903Notes

Reaction equation

HRID 1593903 reaction equation
Cl.C[O:3][C:4](=[O:16])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([F: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]([F: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

Participants

3

Reactant 2

HCID 160906632-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chlorobenzoic acidHCID 68768499(S)-2-amino-3-(3-bromo-4-fluoro-phenyl)-propionic acid methyl ester hydrochloride

Product 1

HCID 45486935(S)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoylamino]-3-(3-bromo-4-fluoro-phenyl)-propionic acid

Procedure

The title compound was prepared from 3-bromo-4-fluoro-L-phenylalanine methyl ester hydrochloride and 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-4-chloro-benzoic acid as in EXAMPLE 1, Part C, followed by hydrolysis of the resulting methyl ester as in EXAMPLE 2, Part E. HPLC: RT=9.72 min. MS (ESI−): mass calcd. for C22H15BrClFN4O5S2, 613.87; m/z found, 611/613 [M−H]−. 1H NMR (400 MHz, CDCl3): 11.36 (s, 1H), 8.34 (d, J=6.9, 1H), 8.16(d, J=8.7, 1H), 7.74-7.67 (m, 1H), 7.66-7.63 (m, 1H), 7.38-7.32 (m, 1H), 7.20-7.15 (m, 1H), 7.12-7.05 (m, 1H), 7.05-6.98 (m, 1H), 6.91-6.84 (m, 1H), 6.68 (d, J=6.7, 1H), 6.09 (s, 2H), 5.04-4.94 (m, 1H), 3.35-3.15 (m, 2H).

Sources & evidence

ORD record
ord-e2c3011102b04fa68d81bd94a25e1292
Source dataset
uspto-grants-2007_11
Patent number
US07297816B2

Reaction notes

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