4-Iodo-2-(quinoxaline-5-sulfonylamino)benzoic acid → (R)-3-(4-Chloro-phenyl)-2-[4-iodo-2-(quinoxaline-5-sulfonylamino)-benzoylamino]-propionic acid
Reaction equation
Cl.C[O:3][C:4](=[O:15])[C@H:5]([NH2:14])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[I:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=[O:22])=[C:19]([NH:26][S:27]([C:30]2[C:31]3[N:32]=[CH:33][CH:34]=[N:35][C:36]=3[CH:37]=[CH:38][CH:39]=2)(=[O:29])=[O:28])[CH:18]=1>>[Cl:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C@@H:5]([NH:14][C:21](=[O:22])[C:20]2[CH:24]=[CH:25][C:17]([I:16])=[CH:18][C:19]=2[NH:26][S:27]([C:30]2[C:31]3[N:32]=[CH:33][CH:34]=[N:35][C:36]=3[CH:37]=[CH:38][CH:39]=2)(=[O:29])=[O:28])[C:4]([OH:3])=[O:15])=[CH:8][CH:9]=1Participants
Procedure
(R)-2-(tert-Butoxycarbonylamino)-3-(4-chloro-phenyl)-propionic acid was treated as in EXAMPLE 2, Part A, to produce (R)-2-amino-3-(4-chloro-phenyl)-propionic acid methyl ester hydrochloride as a white solid. This ester was coupled with 4-iodo-2-(quinoxaline-5-sulfonylamino)-benzoic acid as in EXAMPLE 1, Part C. The resulting methyl ester was hydrolyzed as in EXAMPLE 2, Part E. HPLC: RT=9.74 min. MS (ESI−): mass calcd. for C24H18ClIN4O5S, 635.97; m/z found, 635/637 [M−H]−. 1H NMR (500 MHz, CDCl3): 10.93 (d, J=12.8, 1H), 8.99 (d, J=1.6, 1H), 8.92 (s, 1H), 8.54 (d, J=7.4, 1H), 8.31 (d, J=8.5, 1H), 8.10 (s, 1H), 7.90-7.87 (m, 1H), 7.30-7.22 (m, 3H), 7.05 (d, J=8.4, 2H), 6.84 (d, J=8.2, 1H), 6.29 (d, J=7.9, 1H), 4.93-4.80 (m, 1H), 3.24 (dd, J=14.3, 5.8, 1H), 3.16 (dd, J=14.2, 5.9, 1H).
Sources & evidence
- ORD record
- ord-cfb20c63bd544774b8df6e50faed427d
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855292B2
Reaction notes
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