Hydrochloric Acid → (E)-4-{(4S*,9aR*)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-oxooctahydroquinolizin-4-yl}benzoic acid

HRID 553901Notes

Reaction equation

HRID 553901 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:30]=[CH:31][C:32]=1[N:33]1[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]1)/[CH:8]=[C:9]1/[C:10](=[O:29])[N:11]2[C@@H:16]([CH2:17][CH2:18]/1)[CH2:15][CH2:14][CH2:13][C@H:12]2[C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25]C)=[O:24])=[CH:21][CH:20]=1.Cl>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH:30]=[CH:31][C:32]=1[N:33]1[CH:37]=[C:36]([CH3:38])[N:35]=[CH:34]1)/[CH:8]=[C:9]1/[C:10](=[O:29])[N:11]2[C@@H:16]([CH2:17][CH2:18]/1)[CH2:15][CH2:14][CH2:13][C@H:12]2[C:19]1[CH:28]=[CH:27][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24779885methyl (E)-4-{(4S*,9aR*)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-oxooctahydroquinolizin-4-yl}benzoate

Product 1

HCID 24780024(E)-4-{(4S*,9aR*)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-oxooctahydroquinolizin-4-yl}benzoic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2 N sodium hydroxide solution (1 mL) was added to a solution of methyl (E)-4-{(4S*,9aR*)-7-[3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene]-6-oxooctahydroquinolizin-4-yl}benzoate (80 mg) in methanol (2 mL), and the reaction solution was stirred at room temperature for 18 hours. 2 N hydrochloric acid (1 mL) was added to the reaction solution, and the solution was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: chloroform:methanol=5:1) to obtain 77 mg of the title compound. The property values of the compound are as follows.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. customThe resulting residue was purified by silica gel column chromatography (elution solvent: chloroform:methanol=5:1)

Sources & evidence

ORD record
ord-f9b18b2bec9d46dea9135d61af476da3
Source dataset
uspto-grants-2011_11
Patent number
US08048878B2

Reaction notes

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