Methyl iodide → (S)-2-ethoxy-3-[4-{2-(4-[methylsulfonyl(methyl)amino]phenyl)ethoxy}phenyl]propanoic acid ethyl ester

HRID 987309Notes

Reaction equation

HRID 987309 reaction equation
[CH2:1]([O:3][C:4](=[O:30])[C@@H:5]([O:27][CH2:28][CH3:29])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][S:23]([CH3:26])(=[O:25])=[O:24])=[CH:18][CH:17]=2)=[CH:9][CH:8]=1)[CH3:2].I[CH3:32].[H-].[Na+]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:30])[C@@H:5]([O:27][CH2:28][CH3:29])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]([S:23]([CH3:26])(=[O:25])=[O:24])[CH3:32])=[CH:18][CH:17]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54054668(S)-2-ethoxy-3-[4-{2-(4-[methylsulfonylamino]phenyl)ethoxy}phenyl]propanoic acid ethyl ester

Product 1

HCID 53881407(S)-2-ethoxy-3-[4-{2-(4-[methylsulfonyl(methyl)amino]phenyl)ethoxy}phenyl]propanoic acid ethyl esterYield 55.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-Ethoxy-3-[4-{2-(4-[methylsulfonylamino]phenyl)ethoxy}phenyl]propanoic acid ethyl ester (0.17 g; 0.39 mmole) was dissolved in tetrahydrofuran (10 ml). Iodomethane (0.277 g; 1.95 mmole) and sodium hydride (0.019 g; 0.79 mmole) were added and the reaction mixture was stirred at room temperature for 3 hours and then evaporated. The residue was redissolved and extracted with diethyl ether and water. The organic phase was washed once more with water, dried with sodium sulfate and evaporated. Chromatography with ethyl acetate:petroleum ether (1:1) gave 0.098 g (55.8% yield) of (S)-2-ethoxy-3-[4-{2-(4-[methylsulfonyl(methyl)amino]phenyl)ethoxy}phenyl]propanoic acid ethyl ester.

Workup

  1. customevaporated
  2. dissolutionThe residue was redissolved
  3. extractionextracted with diethyl ether and water
  4. washThe organic phase was washed once more with water
  5. dry with materialdried with sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-1b2dda1d7efa4a8f812bdd9ec70445d0
Source dataset
uspto-grants-2003_10
Patent number
US06630600B1

Reaction notes

Loading…