Water → HCID 17848267, compound

HRID 1352759Notes

Reaction equation

HRID 1352759 reaction equation
[C:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:19](=[O:32])[C:20]2[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=2)=[C:14]([CH:18]=1)[C:15](O)=[O:16])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:34]1C2C=CC=CC=2N=N1.O>CN(C)C=O>[CH2:1]([O:9][C:10]1[CH:18]=[C:14]2[C:13]([C:19]([OH:32])([C:20]3[CH:25]=[C:24]([O:26][CH3:27])[C:23]([O:28][CH3:29])=[C:22]([O:30][CH3:31])[CH:21]=3)[NH:34][C:15]2=[O:16])=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 757711-HydroxybenzotriazoleHCID 17848349HCID 17848349, compound

Product 1

HCID 17848267HCID 17848267, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-benzoyloxy-2-(3,4,5-trimethoxybenzoyl)benzoic acid 50 mg, 14.8M aqueous ammonia 50 μl, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimido hydrochloride 68 mg and 1-hydroxybenzotriazole 15.9 mg is dissolved under ice cooling in N,N-dimethylformamide 2 ml and the mixture is stirred overnight at room temperature. To the reaction mixture is added water. The mixture is extracted with ethyl acetate and the extract is washed with water and dried, followed by removal of the solvent. The residue is purified with silica gel chromatography (solvent: chloroform:ethyl acetate=1:1) and left to be crystallized. The crystals are triturated with diisopropyl ether-ethyl acetate to give 6-benzyloxy-3-hydroxy-3-(3,4,5-trimethoxyphenyl)-2,3-dihydroisoindol-1-one 46.7 mg.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. washthe extract is washed with water
  3. customdried
  4. customfollowed by removal of the solvent
  5. customThe residue is purified with silica gel chromatography (solvent: chloroform:ethyl acetate=1:1)
  6. waitleft
  7. customto be crystallized
  8. customThe crystals are triturated with diisopropyl ether-ethyl acetate

Sources & evidence

ORD record
ord-9d97a9cfeb634b3390a043f6b7d12387
Source dataset
uspto-grants-2007_05
Patent number
US07220736B2

Reaction notes

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