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

HRID 572492

Reaction equation

HRID 572492 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([C:29]3[C:30]([CH3:39])=[C:31]4[C:36](=[CH:37][CH:38]=3)[O:35][CH2:34][CH2:33][CH2:32]4)=[C:14]([CH:21]([O:24][Si](C)(C)C)[C:22]#N)[N:15]([CH3:20])[C:16]2=[O:19])=[CH:11][CH:10]=1)C1C=CC=CC=1.[OH:40]S(O)(=O)=O.[CH3:45][OH:46]>>[CH3:45][O:46][C:22](=[O:40])[CH:21]([OH:24])[C:14]1[N:15]([CH3:20])[C:16](=[O:19])[C:17]2[C:12]([C:13]=1[C:29]1[C:30]([CH3:39])=[C:31]3[C:36](=[CH:37][CH:38]=1)[O:35][CH2:34][CH2:33][CH2:32]3)=[CH:11][CH:10]=[C:9]([OH:8])[CH:18]=2

Participants

3

Reactant 2

HCID 18363649Sulfuric acid methanolHCID 68295398[7-Benzyloxy-2-methyl-4-(5-methyl-chroman-6-yl)-1-oxo-1,2-dihydro-isoquinolin-3-yl]-trimethylsilanyloxy-acetonitrile

Product 1

HCID 68295427Hydroxyl-[7-hydroxy-2-methyl-4-(5-methyl-chroman-6-yl)-1-oxo-1,2-dihydro-isoquinolin-3-yl]-acetic acid methyl esterYield 32%

Conditions

Temperature
80 °C

Procedure

To a solution of [7-Benzyloxy-2-methyl-4-(5-methyl-chroman-6-yl)-1-oxo-1,2-dihydro-isoquinolin-3-yl]-trimethylsilanyloxy-acetonitrile (2.5 g, 4.64 mmol) in H2SO4/CH3OH (30 mL, V/V=1:3). The resulting mixture was heated to 80° C. under N2 for 12 h. The reaction mixture was poured into ice water and extracted with DCM (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 (0.6 g, 32%). LCMS (10-80 AB—2MIN.M): Rt=0.993, purity=75%, M+1=410.

Workup

  1. extractionextracted with DCM (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-91366163d735410ab77b5c8dfa683333
Source dataset
uspto-grants-2015_05
Patent number
US09029391B2

Linked notes

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