2-[(2,1,3-Benzothiadiazol-4-ylsulfonyl)amino]-5-chlorobenzoic acid → (r)-2-[2-(Benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-benzoylamino]-3-(4-chloro-phenyl)-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.[N:16]1[S:20][N:19]=[C:18]2[C:21]([S:25]([NH:28][C:29]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:30]=3[C:31](O)=[O:32])(=[O:27])=[O:26])=[CH:22][CH:23]=[CH:24][C:17]=12>>[N:16]1[S:20][N:19]=[C:18]2[C:21]([S:25]([NH:28][C:29]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:30]=3[C:31]([NH:14][C@H:5]([CH2:6][C:7]3[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=3)[C:4]([OH:3])=[O:15])=[O:32])(=[O:27])=[O:26])=[CH:22][CH:23]=[CH:24][C:17]=12Participants
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 2-(benzo[1,2,5]thiadiazole-4-sulfonylamino)-5-chloro-benzoic acid 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=10.28 min. MS (ESI−): mass calcd. for C22H16Cl2N4O5S2, 549.99; m/z found, 549/551 [M−H]−. 1H NMR (500 MHz, CDCl3): 10.92 (s, 1H), 8.30 (d, J=7.0, 1H), 8.19 (d, J=8.8, 1H), 7.70-7.66 (m, 1H), 7.64 (d, J=9.0, 1H), 7.31-7.26 (m, 3H), 7.14 (d, J=2.3, 1H), 7.08 (d, J=8.3, 2H), 6.38 (d, J=7.3, 1H), 5.00-4.96 (m, 1H), 3.29 (dd, J=14.3, 5.7, 1H), 3.20 (dd, J=14.2, 5.8, 1H).
Sources & evidence
- ORD record
- ord-efb737727d8c4bc2b45111706e89d9fd
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07855292B2
Reaction notes
Loading…