Sodium Hydroxide → 2-[4-[2-(2-Benzothiazolyl)vinyl]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetic acid
Reaktionsgleichung
[OH-].[Na+].[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH:12]=[CH:13][C:14]1[CH:48]=[CH:47][C:17]([C:18]([NH:20][C:21]2[CH:33]=[C:32]([CH2:34][CH2:35][CH2:36][S:37]([C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[CH:31]=[CH:30][C:22]=2[O:23][CH2:24][C:25]([O:27]CC)=[O:26])=[O:19])=[CH:16][CH:15]=1>O1CCCC1>[S:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[CH:12]=[CH:13][C:14]1[CH:15]=[CH:16][C:17]([C:18]([NH:20][C:21]2[CH:33]=[C:32]([CH2:34][CH2:35][CH2:36][S:37]([C:40]3[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[CH:31]=[CH:30][C:22]=2[O:23][CH2:24][C:25]([OH:27])=[O:26])=[O:19])=[CH:47][CH:48]=1Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
10% Sodium hydroxide aqueous solution (6 ml) was added at room temperature to a mixture of ethyl 2-[4-[2-(2-benzothiazolyl)vinyl]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetate (196 mg, 0.29 mmol) and tetrahydrofuran (10 ml), and the reaction solution was stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure, water was added the resulting residue, and then the solution was adjusted to pH 1 by adding concentrated hydrochloric acid. Thereafter, the solid material formed was collected by filtration, washed with water and ether in that order, dried under reduced pressure and then recrystallized from ethanol (50 ml) to give 2-[4-[2-(2-benzothiazolyl)vinyl]benzoylamino]-4-[3-(4-chlorophenylsulfonyl)propyl]phenoxyacetic acid (156 mg, 0.24 mmol, 83%) as colorless crystals.