Water → HCID 68474347, compound

HRID 387652Notes

Reaction equation

HRID 387652 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8]([C:24]([O:26][CH3:27])=[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].[H-].[Na+].I[CH3:31].O>CN(C)C=O.C(OCC)(=O)C>[CH3:31][N:5]([S:2]([CH3:1])(=[O:3])=[O:4])[C:6]1[CH:7]=[C:8]([C:24]([O:26][CH3:27])=[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

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68470577HCID 68470577, compound

Product 1

HCID 68474347HCID 68474347, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.4 g of methyl 7-[(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate is dissolved under an inert atmosphere in 18 cm3 of dimethylformamide at a temperature close to 20° C. This solution is cooled to a temperature close to 0° C., then 141 mg of sodium hydride (60% in oil) are added in 2 lots. The reaction mixture is stirred for 2 h at a temperature close to 0° C. 0.264 cm3 of iodomethane is introduced then the stirring is continued for 20 h while gradually allowing it to climb back up to a temperature close to 20° C. 20 cm3 of iced water and 50 cm3 of ethyl acetate are added to the reaction mixture. After decanting, the organic phase is washed with 20 cm3 of a 2M aqueous solution of hydrochloric acid, 3 lots of 20 cm3 of water then 30 cm3 of a saturated aqueous solution of sodium chloride. It is then dried over magnesium sulfate, filtered then concentrated using a rotary evaporator under reduced pressure (5 kPa). 1.187 g of methyl 7-[methyl(methylsulfonyl)amino]-1-oxo-2-(1-propylbutyl)-1,2,3,4-tetrahydroisoquinoline-5-carboxylate are obtained in the form of beige crystals.

Workup

  1. customclose to 20° C
  2. temperatureThis solution is cooled to a temperature
  3. customclose to 0° C.
  4. customclose to 0° C
  5. waitthe stirring is continued for 20 h
  6. customclose to 20° C
  7. customAfter decanting
  8. washthe organic phase is washed with 20 cm3 of a 2M aqueous solution of hydrochloric acid, 3 lots of 20 cm3 of water
  9. dry with materialIt is then dried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationthen concentrated
  12. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-1cfdf40a71554d7d8a4618d1de0e0a2b
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

Loading…