4-Chloro-2-(quinoxaline-5-sulfonylamino)benzoic acid → (+/-)-2-[4-Chloro-2-(quinoxaline-5-sulfonylamino)-benzoylamino]-3-(3,4-dichloro-phenyl)-3-oxo-propionic acid methyl ester
Reaction equation
[Cl: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.[CH3:26][O:27][C:28](=[O:41])[CH:29]([NH2:40])[C:30]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=1)=[O:31]>>[CH3:26][O:27][C:28](=[O:41])[CH:29]([NH:40][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Cl:1])=[CH:3][C:4]=1[NH:11][S:12]([C:15]1[C:16]2[N:17]=[CH:18][CH:19]=[N:20][C:21]=2[CH:22]=[CH:23][CH:24]=1)(=[O:14])=[O:13])[C:30]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=1)=[O:31]Participants
3
Reactant 2
Product 1
Procedure
4-Chloro-2-(quinoxaline-5-sulfonylamino)-benzoic acid was coupled to (±)-2-amino-3-(3,4-dichloro-phenyl)-3-oxo-propionic acid methyl ester hydrochloride as in EXAMPLE 1, Part C. HPLC: RT=10.65 min. MS (ESI+): mass calcd. for C25H17Cl3N4O6S, 605.99; m/z found, 607/609 [M+H]+. 1H NMR (500 MHz, CDCl3): 11.23 (s, 1H), 8.88 (d, J=1.8, 1H), 8.85 (d, J=1.8, 1H), 8.58 (dd, J=7.4, 1.4, 1H), 8.32 (dd, J=8.5, 1.4, 1H), 8.24 (d, 2.1, 1H), 8.03 (dd, J=8.4, 2.1, 1H), 7.89-7.86 (m, 1H), 7.79 (d, J=2.0, 1H), 7.69 (d, J=8.4, 1H), 7.45 (d, J=8.5, 1H), 7.30 (d, J=6.9, 1H), 6.97 (dd, J=8.4, 2.0, 1H), 6.19 (d, J=6.9, 1H), 3.78 (s, 3H).
Sources & evidence
- ORD record
- ord-84fa9733b0854a469eb57655ada0dfbd
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855292B2
Reaction notes
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