1,4-Dioxane hydrochloride → 6-carbamoyl-2-(4-carboxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

HRID 750257Notes

Reaction equation

HRID 750257 reaction equation
O1CCOCC1.Cl.[CH3:8][O:9][C:10]([C:12]1[N:13]([CH2:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([O:41]C(C)(C)C)=[O:40])=[CH:35][CH:34]=2)[C:14](=[O:31])[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])[NH2:29])=[CH:17][CH:16]=2)=[O:11]>>[CH3:8][O:9][C:10]([C:12]1[N:13]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([C:39]([OH:41])=[O:40])=[CH:37][CH:38]=2)[C:14](=[O:31])[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])[NH2:29])=[CH:17][CH:16]=2)=[O:11]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 691570372-(4-tert-butoxycarbonylbenzyl)-6-carbamoyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl Ester

Product 1

HCID 691567496-carbamoyl-2-(4-carboxybenzyl)-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic Acid Methyl EsterYield 69%

Procedure

To a 4N-hydrochloric acid dioxane solution (5 ml) was added 2-(4-tert-butoxycarbonylbenzyl)-6-carbamoyl-1-oxo-4-phenyl-1,2-dihydroisoquinoline-3-carboxylic acid methyl ester (140 mg), and the mixture was stirred at room temperature for 2 hrs. The reaction mixture was concentrated under reduced pressure, and the obtained crystals were washed with methanol to give the title compound (86 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. washthe obtained crystals were washed with methanol

Sources & evidence

ORD record
ord-d49cd52b741947b0b91ed9626f7ae955
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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