Sodium Hydroxide → 3-{3-[(5-Benzoyl-furan-2-carbonyl)-amino]-phenyl}-acrylic acid
Reaction equation
C([O:3][C:4](=[O:29])[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([C:16]2[O:17][C:18]([C:21](=[O:28])[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:19][CH:20]=2)=[O:15])[CH:8]=1)C.[OH-].[Na+]>CCO>[C:21]([C:18]1[O:17][C:16]([C:14]([NH:13][C:9]2[CH:8]=[C:7]([CH:6]=[CH:5][C:4]([OH:29])=[O:3])[CH:12]=[CH:11][CH:10]=2)=[O:15])=[CH:20][CH:19]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
4
Procedure
The ester (10) (28 mg, 0.072 mmol) was hydrolysed using Method C, except that EtOH (0.15 mL) and 1M NaOH (0.15 mL) were used. After the reaction, the solvent was removed under a stream of nitrogen gas and the residue acidified to pH 5 using 1N HCl. The precipitate was filtered off and dried to give the title compound. Yield: 8 mg, 31%; LC-MS tr 1.95 min; HPLC Purity: 98%; MS (ES+) m/z 362 (M+H); 1H NMR (400 MHz; DMSO): δ 6.4 (d, 1H), 7.10 (d, 1H), 7.20-7.40 (m, 2H), 7.55 (m, 1H), 7.60-7.80 (m, 3H), 7.80-7.90 (d, 1H), 7.95 (s, 1H), 7.95-8.10 (m, 3H)