Hydrochloric Acid → 8-(4-(((5-Fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzamido)octanoic acid
Reaction equation
C[O:2][C:3](=[O:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:33])[C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[N:20][N:21]=[C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[C:28]([F:31])[CH:29]=3)[NH:24][C:23]2=[O:32])=[CH:15][CH:14]=1.CO.[Li+].[OH-].Cl>O>[F:31][C:28]1[CH:29]=[C:30]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:32])[C:22]2=[N:21][N:20]=[CH:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:34])=[O:2])=[O:33])=[CH:18][CH:17]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
8-(4-(((5-fluoro-2-oxoindolin-3-ylidene)hydrazono)methyl)benzamido)octanoic acid methyl ester (466 mg, 1 mmol) and 300ml of CH3OH were stirred at room temperature while 25 ml of 4 N solution of LiOH in H2O was added. The mixture was stirred for 24 hours at room temperature. The mixture is neutralized with concentrated hydrochloric acid to pH 7 and evaporated under vacuum to remove methanol. The residue was adjusted to pH 3 with concentrated hydrochloric acid. The solids were collected by vacuum filtration, washed with water and dried under vacuum to give the title compound (149 mg, 33% yield) as a brown solid. LC-MS (m/z) 453 (M+1).
Workup
- additionwas added
- customevaporated under vacuum
- customto remove methanol
- filtrationThe solids were collected by vacuum filtration
- washwashed with water
- customdried under vacuum
Sources & evidence
- ORD record
- ord-33152822c10d40a9a63db692888b8220
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07863315B2
Reaction notes
Loading…