4-Iodo-2-(quinoxaline-5-sulfonylamino)benzoic acid → (S)-3-(3,4-Dichloro-phenyl)-2-[4-iodo-2-(quinoxaline-5-sulfonylamino)-benzoylamino]-propionic acid
Reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([NH:11][S:12]([C:15]2[C:16]3[N:17]=[CH:18][CH:19]=[N:20][C:21]=3[CH:22]=[CH:23][CH:24]=2)(=[O:14])=[O:13])[CH:3]=1.Cl.C[O:27][C:28](=[O:40])[C@@H:29]([NH2:39])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1>>[Cl:38][C:33]1[CH:32]=[C:31]([CH2:30][C@H:29]([NH:39][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][C:2]([I:1])=[CH:3][C:4]=2[NH:11][S:12]([C:15]2[C:16]3[N:17]=[CH:18][CH:19]=[N:20][C:21]=3[CH:22]=[CH:23][CH:24]=2)(=[O:14])=[O:13])[C:28]([OH:27])=[O:40])[CH:36]=[CH:35][C:34]=1[Cl:37]Participants
3
Procedure
4-Iodo-2-(quinoxaline-5-sulfonylamino)-benzoic acid was coupled with (S)-2-amino-3-(3,4-dichloro-phenyl)-propionic acid methyl ester hydrochloride as in Example 1, Part C. The resulting methyl ester was hydrolyzed as in EXAMPLE 2, Part E, to afford the title compound. HPLC: RT=10.05 min. MS (ESI−): mass calcd. for C24H17Cl2IN4O5S, 671.29; m/z found, 669/671 [M−H]−. 1H NMR (500 MHz, CDCl3): 10.86 (s, 1H), 9.01 (d, J=1.6, 1H), 8.92 (d, J=1.6, 1H), 8.55 (dd, J=7.3, 1.0, 1H), 8.32 (dd, J=8.5, 1.0, 1H), 8.08 (d, J=1.3, 1H), 7.91-7.88 (m, 1H), 7.34 (d, J=8.2, 1H), 7.30-7.24 (m, 2H), 6.98 (dd, J=8.2, 1.9, 1H), 6.88 (d, J=8.2, 1H), 6.38 (d, J=7.3, 1H), 4.90 (q, J=5.9, 1H), 3.28-3.12 (m, 2H).
Sources & evidence
- ORD record
- ord-f8a880f30acb440ca1e1b808a56d69b7
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855292B2
Reaction notes
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