Sodium Hydroxide → 7-(2-Oxazolyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid

HRID 387670Notes

Reaction equation

HRID 387670 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([C:24]([O:26]C)=[O:25])[C:9]2[CH2:10][CH2:11][N:12]([CH:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[C:13](=[O:16])[C:14]=2[CH:15]=1.[OH-].[Na+]>O1CCOCC1>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([C:24]([OH:26])=[O:25])[C:9]2[CH2:10][CH2:11][N:12]([CH:17]([CH2:18][CH2:19][CH3:20])[CH2:21][CH2:22][CH3:23])[C:13](=[O:16])[C:14]=2[CH:15]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68472426HCID 68472426, compound

Product 1

HCID 684696977-(2-Oxazolyl)-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acidYield 93.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

320 mg of methyl 7-(2-oxazolyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are dissolved in 7 cm3 of dioxane at a temperature close to 20° C. 2.1 cm3 of a 1N aqueous solution of sodium hydroxide are added, then the reaction mixture is heated at a temperature close to 60° C. for 30 min. The dioxane contained in the reaction mixture is concentrated to dryness under reduced pressure (5 kPa). 2.5 cm3 of a 1N aqueous solution of hydrochloric acid, 20 cm3 of dichloromethane and 20 cm3 of water are added to the residue obtained. After decanting, the organic phase is dried over anhydrous magnesium sulfate, filtered and concentrated to dryness under reduced pressure (5 kPa). 289 mg of 7-(2-oxazolyl]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid are obtained in the form of a beige powder.

Workup

  1. customclose to 20° C
  2. temperaturethe reaction mixture is heated at a temperature
  3. customclose to 60° C. for 30 min
  4. concentrationis concentrated to dryness under reduced pressure (5 kPa)
  5. addition2.5 cm3 of a 1N aqueous solution of hydrochloric acid, 20 cm3 of dichloromethane and 20 cm3 of water are added to the residue
  6. customobtained
  7. customAfter decanting
  8. dry with materialthe organic phase is dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to dryness under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-01fb23fbfef34a3d9a2584a3405dd423
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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