Sodium Hydroxide → HCID 68469685, compound

HRID 387653Notes

Reaction equation

HRID 387653 reaction equation
[CH3:1][N:2]([S:25]([CH3:28])(=[O:27])=[O:26])[C:3]1[CH:4]=[C:5]([C:21]([O:23]C)=[O:22])[C:6]2[CH2:7][CH2:8][N:9]([CH:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[C:10](=[O:13])[C:11]=2[CH:12]=1.[OH-].[Na+]>O1CCOCC1>[CH3:1][N:2]([S:25]([CH3:28])(=[O:26])=[O:27])[C:3]1[CH:4]=[C:5]([C:21]([OH:23])=[O:22])[C:6]2[CH2:7][CH2:8][N:9]([CH:14]([CH2:18][CH2:19][CH3:20])[CH2:15][CH2:16][CH3:17])[C:10](=[O:13])[C:11]=2[CH:12]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68474347HCID 68474347, compound

Product 1

HCID 68469685HCID 68469685, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

0.25 g of methyl 7-[methyl(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate is dissolved in 5 cm3 of dioxane at a temperature close to 20° C. 1.52 cm3 of a 1M aqueous solution of sodium hydroxide are added, then the reaction mixture is heated at a temperature close to 60° C. for 1 h. The dioxane contained in the reaction mixture is concentrated using a rotary evaporator under reduced pressure (5 kPa). 20 cm3 of ethyl ether and 10 cm3 of water are added to the residue obtained. After decanting, the aqueous phase is acidified with 1.6 cm3 of a 1M aqueous solution of hydrochloric acid. The aqueous phase is extracted with 20 cm3 of dichloromethane. After decanting, the organic phase is dried over magnesium sulfate, filtered then concentrated using a rotary evaporator under reduced pressure (5 kPa). 0.233 g of 7-[methyl(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid is obtained in the form of a pale pink powder.

Workup

  1. customclose to 20° C
  2. temperaturethe reaction mixture is heated at a temperature
  3. customclose to 60° C. for 1 h
  4. concentrationis concentrated
  5. customa rotary evaporator under reduced pressure (5 kPa)
  6. addition20 cm3 of ethyl ether and 10 cm3 of water are added to the residue
  7. customobtained
  8. customAfter decanting
  9. extractionThe aqueous phase is extracted with 20 cm3 of dichloromethane
  10. customAfter decanting
  11. dry with materialthe organic phase is dried over magnesium sulfate
  12. filtrationfiltered
  13. concentrationthen concentrated
  14. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-e33ccca63d5b4bd3ab2efcd8bb72f1b5
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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