Hydroxyl-[7-hydroxy-2-methyl-4-(5-methyl-chroman-6-yl)-1-oxo-1,2-dihydro-isoquinolin-3-yl]-acetic acid methyl ester → methane;methyl 2-[7-hydroxy-2-methyl-4-(5-methyl-3,4-dihydro-2H-chromen-6-yl)-1-oxoisoquinolin-3-yl]-2-[(2-methylpropan-2-yl)oxy]acetate

HRID 572493Notes

Reaction equation

HRID 572493 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH:4]([OH:29])[C:5]1[N:6]([CH3:28])[C:7](=[O:27])[C:8]2[C:13]([C:14]=1[C:15]1[C:16]([CH3:25])=[C:17]3[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=[C:10]([OH:26])[CH:9]=2>C(OC(C)=O)(C)(C)C.O>[CH4:1].[CH3:1][O:2][C:3](=[O:30])[CH:4]([O:29][C:8]([CH3:13])([CH3:9])[CH3:7])[C:5]1[N:6]([CH3:28])[C:7](=[O:27])[C:8]2[C:13]([C:14]=1[C:15]1[C:16]([CH3:25])=[C:17]3[C:22](=[CH:23][CH:24]=1)[O:21][CH2:20][CH2:19][CH2:18]3)=[CH:12][CH:11]=[C:10]([OH:26])[CH:9]=2

Participants

4

Reactant 1

HCID 68295427Hydroxyl-[7-hydroxy-2-methyl-4-(5-methyl-chroman-6-yl)-1-oxo-1,2-dihydro-isoquinolin-3-yl]-acetic acid methyl ester

Product 1

HCID 86700720methane;methyl 2-[7-hydroxy-2-methyl-4-(5-methyl-3,4-dihydro-2H-chromen-6-yl)-1-oxoisoquinolin-3-yl]-2-[(2-methylpropan-2-yl)oxy]acetateYield 85%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 10908tert-Butyl acetateSolvent

Procedure

To a solution of Hydroxyl-[7-hydroxy-2-methyl-4-(5-methyl-chroman-6-yl)-1-oxo-1,2-dihydro-isoquinolin-3-yl]-acetic acid methyl ester (600 mg, 1.465 mmol) in t-BuOAc (10 ml) was added HClO4 (512 mg, 5.12 mmol). The resultant mixture was stirred at RT under N2 for 2 h. The reaction mixture was diluted with water and extracted with EA (50 mL*3), dried over sodium sulfate and concentrated to dryness. The mixture was purified by chromatography column on silica gel to afford the title product (300 mg, 44%). LCMS (10-80 AB—2MIN.M): Rt=1.308, purity=96%, M+1=466.

Workup

  1. extractionextracted with EA (50 mL*3)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated to dryness
  4. customThe mixture was purified by chromatography column on silica gel

Sources & evidence

ORD record
ord-4e3820a1dee84e64a68ca625bbb1ceb2
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Reaction notes

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