Methyl 2-benzamido-2-(4-methoxycarbonyl-3-methoxy-6-methylphenyl)acetate → 4-(amino-carboxy-methyl)-2-hydroxy-5-methyl-benzoic Acid
Reaction equation
C([NH:9][CH:10]([C:15]1[C:20]([CH3:21])=[CH:19][C:18]([C:22]([O:24]C)=[O:23])=[C:17]([O:26]C)[CH:16]=1)[C:11]([O:13]C)=[O:12])(=O)C1C=CC=CC=1>Cl>[C:22]([C:18]1[CH:19]=[C:20]([CH3:21])[C:15]([CH:10]([C:11]([OH:13])=[O:12])[NH2:9])=[CH:16][C:17]=1[OH:26])([OH:24])=[O:23]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A stirred suspension of methyl 2-benzamido-2-(4-methoxycarbonyl-3-methoxy-6-methylphenyl)acetate (120 mg, 0.32 mmol) in aqueous hydrochloric acid (5M, 3 ml) was heated to 110° C. for 7 days in a PTFE lined stainless steel sealed reaction vessel. The contents were periodically cooled, evaporated and topped up with an equivalent amount of fresh aqueous hydrochloric acid. The contents were cooled and chromatographed on ion exchange resin following the procedure described in Example 1 (iii) to give the title compound as an off-white solid, m.p. >250° C.