Hydrochloric Acid → HCID 68471216, compound

HRID 387666Notes

Reaction equation

HRID 387666 reaction equation
[CH3:1][S:2]([NH:5][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)(=[O:4])=[O:3].[OH-].[Na+].Cl.ClCCl>O1CCOCC1>[CH3:1][S:2]([NH:5][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)(=[O:3])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 68470577HCID 68470577, compound

Product 1

HCID 68471216HCID 68471216, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

0.51 g of methyl 7-[(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate is dissolved in 10.5 cm3 of dioxane at a temperature close to 20° C. 3.2 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). 20 cm3 of ethyl ether and 20 cm3 of water are added to the residue obtained. After decantation, the aqueous phase is acidified with 2 cm3 of a 2N aqueous solution of hydrochloric acid. 50 cm3 of dichloromethane are added to the mixture, which is stirred for 1 h at a temperature close to 20° C. The precipitate is filtered, washed with two lots of 10 cm3 of water then two lots of 10 cm3 of dichloromethane and dried under vacuum. 0.42 g of 7-[(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylic acid is obtained in the form of a 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. addition20 cm3 of ethyl ether and 20 cm3 of water are added to the residue
  6. customobtained
  7. customclose to 20° C
  8. filtrationThe precipitate is filtered
  9. washwashed with two lots of 10 cm3 of water
  10. dry with materialtwo lots of 10 cm3 of dichloromethane and dried under vacuum

Sources & evidence

ORD record
ord-16a6ab1ee6274505b05135dbeed8eb2d
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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