Hydrochloric Acid → HCID 58494595, compound

HRID 516236Notes

Reaction equation

HRID 516236 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][C:7]1[C:16]([CH3:17])=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:18])[NH:14]2)=[CH:9][C:8]=1[CH2:19][CH2:20]C(OCC)=O.[OH-:26].[Na+].Cl>CCO.C1COCC1>[CH3:1][O:2][CH2:3][O:4][CH2:5][CH2:6][C:7]1[C:16]([CH3:17])=[C:15]2[C:10]([CH2:11][CH2:12][C:13](=[O:18])[NH:14]2)=[CH:9][C:8]=1[CH2:19][CH2:20][NH:14][C:13](=[O:18])[O:26][C:7]([CH3:16])([CH3:8])[CH3:6]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58494774HCID 58494774, compound

Product 1

HCID 58494595HCID 58494595, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 10.81 g of ethyl 3-{7-[2-(methoxymethoxy)ethyl]-8-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl}propanoate in 100 ml of EtOH and 100 ml of THF was added 100 ml of a 1 M aqueous sodium hydroxide solution, followed by stirring at room temperature for 1 hour. The reaction mixture was neutralized by the addition of hydrochloric acid and then concentrated under reduced pressure to one third of the liquid amount, and the residue was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. To a solution of the resulting residue in 300 ml of t-butanol were added 9.0 ml of triethylamine and 7.0 ml of DPPA, followed by heating and refluxing for 24 hours. The reaction mixture was concentrated under reduced pressure, the residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc), and then the resulting solid was washed with HEX to obtain 8.006 g of t-butyl (2-{7-[2-(methoxymethoxy)ethyl]-8-methyl-2-oxo-1,2,3,4-tetrahydroquinolin-6-yl}ethyl)carbamate as a milky white solid.

Workup

  1. concentrationconcentrated under reduced pressure to one third of the liquid amount
  2. extractionthe residue was extracted with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo a solution of the resulting residue in 300 ml of t-butanol were added 9.0 ml of triethylamine and 7.0 ml of DPPA
  7. temperatureby heating
  8. temperaturerefluxing for 24 hours
  9. concentrationThe reaction mixture was concentrated under reduced pressure
  10. customthe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)
  11. washthe resulting solid was washed with HEX

Sources & evidence

ORD record
ord-e17f29690902411483995788601f2a7a
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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