Hydrogen chloride-ethyl acetate → 2-(4-carboxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic Acid Dimethyl Ester

HRID 750254Notes

Reaction equation

HRID 750254 reaction equation
C(OC(=O)C)C.Cl.[CH3:8][O:9][C:10]([C:12]1[N:13]([CH2:33][C:34]2[CH:39]=[CH:38][C:37]([C:40]([O:42]C(C)(C)C)=[O:41])=[CH:36][CH:35]=2)[C:14](=[O:32])[C:15]2[C:20]([C:21]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:19][C:18]([C:28]([O:30][CH3:31])=[O:29])=[CH:17][CH:16]=2)=[O:11]>>[CH3:8][O:9][C:10]([C:12]1[N:13]([CH2:33][C:34]2[CH:35]=[CH:36][C:37]([C:40]([OH:42])=[O:41])=[CH:38][CH:39]=2)[C:14](=[O:32])[C:15]2[C:20]([C:21]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[CH:19][C:18]([C:28]([O:30][CH3:31])=[O:29])=[CH:17][CH:16]=2)=[O:11]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 691568282-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic Acid Dimethyl Ester

Product 1

HCID 691571542-(4-carboxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic Acid Dimethyl EsterYield 89.5%

Procedure

To a 4N-hydrochloric acid ethyl acetate solution (4 ml) was added 2-(4-tert-butoxycarbonylbenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3,6-dicarboxylic acid dimethyl ester (200 mg), and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated and crystals were washed with a mixture of ethyl acetate and hexane to give the title compound (160 mg).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washcrystals were washed with a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-85a6b87ec098463699f2442394de57cc
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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