Hydrochloric Acid → HCID 22175954, compound

HRID 1797710Notes

Reaction equation

HRID 1797710 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13]([C:24]([O:26]C)=[O:25])=[C:12]2[C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[OH-].[Li+].Cl>CO.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=[O:19])[N:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[C:13]([C:24]([OH:26])=[O:25])=[C:12]2[C:28]1[S:29][CH:30]=[CH:31][CH:32]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 22176104HCID 22176104, compound

Product 1

HCID 22175954HCID 22175954, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

To a suspension of methyl 6-(benzyloxy)-2-isobutyl-1-oxo-4-(2-thienyl)-1,2-dihydro-3-isoquinolinecarboxylate (2.01 g, 4.5 mmol) in methanol (30 ml) was added a solution of lithium hydroxide monohydrate (0.57 g, 13.5 mmol) in water (10 ml). The resulting mixture was refluxed under heating for 48 h. The reaction mixture was poured into water, acidified with 1N hydrochloric acid and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting crystals were recrystallized from ethyl acetate-n-hexane to give 6-(benzyloxy)-2-isobutyl-1-oxo-4-(2-thienyl)-1,2-dihydro-3-isoquinolinecarboxylic acid (1.71 g, 87.7%) as crystals.

Workup

  1. temperatureThe resulting mixture was refluxed
  2. temperatureunder heating for 48 h
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crystals were recrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-9eab661a694344808a295ea7d4e30a5a
Source dataset
uspto-grants-2006_04
Patent number
US07034039B2

Reaction notes

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