Lithium hydroxide, monohydrate → 2-(2-Carboxy-2-(4-((triisopropylsilyloxy)methyl)phenyl)ethylcarbamoyl)benzoic acid
Reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH:13]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][O:25][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28])=[CH:20][CH:19]=1)[C:14]([O:16]C)=[O:15].[OH:36][Li].O>C1COCC1.O>[C:14]([CH:13]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][O:25][Si:26]([CH:30]([CH3:32])[CH3:31])([CH:33]([CH3:34])[CH3:35])[CH:27]([CH3:29])[CH3:28])=[CH:22][CH:23]=1)[CH2:12][NH:3][C:2]([C:10]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:4]([OH:11])=[O:36])=[O:1])([OH:16])=[O:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To methyl 3-(1,3-dioxoisoindolin-2-yl)-2-(4-((triisopropylsilyloxy)methyl)phenyl)propanoate (E134) in THF/H2O was added LiOH.H2O, and the solution was stirred for 1.5 h or until conversion to product was visible by LC-MS. The solution was then poured into EtOAc/NH4Cl(sat)/1 N HCl (3:1) and the aqueous layer was further extracted with EtOAc. The organics were dried (MgSO4), filtered, and evaporated to give crude 2-(2-carboxy-2-(4-((triisopropylsilyloxy)methyl)phenyl)ethylcarbamoyl)benzoic acid (E135).