Water → HCID 71246507, compound

HRID 1519092Notes

Reaction equation

HRID 1519092 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:20])([NH:6][S:7]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)(=[O:9])=[O:8])[CH3:5].[CH3:22]I.O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:5])([N:6]([CH3:22])[S:7]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[CH:17][CH:16]=[CH:15]2)(=[O:9])=[O:8])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 71246852HCID 71246852, compound

Product 1

HCID 71246507HCID 71246507, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

methyl-2-methyl-2-(quinoline-8-sulfonamido)propanoate (699 mg, 2.26 mmol) was dissolved in DMF (10 ml), added with MeI (0.49 ml, 7.93 mmol) at 0° C., and stirred at room temperature for 12 hours. The resultant solution was added with H2O and extracted with EA (×2). The organic solution was washed with H2O, dried with MgSO4, and filtered. Through vacuum distillation, the solvent was removed. The resultant mixture was purified with column chromatography so as to obtain methyl-2-methyl-2-(N-methylquinoline-8-sulfonamido)propanoate (694 mg, 2.15 mmol, 95%).

Workup

  1. extractionextracted with EA (×2)
  2. washThe organic solution was washed with H2O
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. distillationThrough vacuum distillation
  6. customthe solvent was removed
  7. customThe resultant mixture was purified with column chromatography so as

Sources & evidence

ORD record
ord-e920dfa3495d438ead3172d89a00fba5
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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