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

HRID 750259Notes

Reaction equation

HRID 750259 reaction equation
C(OC(=O)C)C.Cl.[CH3:8][O:9][C:10]([C:12]1[N:13]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([O:43]C(C)(C)C)=[O:42])=[CH:37][CH:36]=2)[C:14](=[O:33])[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:32])[N:29]([CH3:31])[CH3:30])=[CH:17][CH:16]=2)=[O:11]>>[CH3:8][O:9][C:10]([C:12]1[N:13]([CH2:34][C:35]2[CH:36]=[CH:37][C:38]([C:41]([OH:43])=[O:42])=[CH:39][CH:40]=2)[C:14](=[O:33])[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:32])[N:29]([CH3:30])[CH3:31])=[CH:17][CH:16]=2)=[O:11]

Participants

3

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 691567922-(4-tert-butoxycarbonylbenzyl)-6-dimethylcarbamoyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

Product 1

HCID 691563372-(4-carboxybenzyl)-6-dimethylcarbamoyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterYield 68.5%

Procedure

To a 4N-hydrochloric acid ethyl acetate solution (4 ml) was added 2-(4-tert-butoxycarbonylbenzyl)-6-dimethylcarbamoyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (140 mg), and the mixture was stirred at room temperature for 4 hrs. The reaction mixture was concentrated under reduced pressure, and the obtained residue was crystallized from methanol-diisopropyl ether to give the title compound (86 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was crystallized from methanol-diisopropyl ether

Sources & evidence

ORD record
ord-ad8dcc0bdc6f40cbb3234a96ac85daf0
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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