Water → 2-{3-[4-(2-Methyl-2-morpholin-4-yl-propionyl)-phenylthio]-propylthiomethyl}-acrylic acid methyl ester

HRID 1838491Notes

Reaction equation

HRID 1838491 reaction equation
[SH:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[C:13]([CH3:21])([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH3:14])=[CH:8][CH:7]=1.Br[CH2:24][C:25](=[CH2:30])[C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+].O>CO>[CH3:29][O:28][C:26](=[O:27])[C:25]([CH2:30][S:1][CH2:2][CH2:3][CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:22])[C:13]([CH3:14])([N:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)[CH3:21])=[CH:8][CH:7]=1)=[CH2:24]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 5210932-Propenoic acid, 2-(bromomethyl)-, methyl esterHCID 109477861-[4-(3-Mercaptopropylthio)phenyl]-2-methyl-2-morpholin-4-yl-propane-1-one

Product 1

HCID 538148112-{3-[4-(2-Methyl-2-morpholin-4-yl-propionyl)-phenylthio]-propylthiomethyl}-acrylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3.0 g (8.8 mmol) of 1-[4-(3-mercaptopropylthio)phenyl]-2-methyl-2-morpholin-4-yl-propane-1-one are dissolved in 1.50 ml of methanol. To the solution are successively added 1.89 g (10.6 mmol) of methyl 2-(bromomethyl)acrylate and 1.22 g (8.8 mmol) of potassium carbonate, and the reaction mixture is stirred at room temperature for 10 min. The reaction mixture is poured into water and extracted with ethyl acetate. The organic phase is washed with water, and dried over MgSO4. After distilling off the ethyl acetate, the residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3) as an eluent, and an oily product is obtained.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase is washed with water
  3. dry with materialdried over MgSO4
  4. distillationAfter distilling off the ethyl acetate
  5. customthe residue is purified by means of column chromatography on silica gel with ethyl acetate-hexane (1:3) as an eluent
  6. customan oily product is obtained

Sources & evidence

ORD record
ord-9a6d97723252457abe296f65fd4b13d1
Source dataset
uspto-grants-2004_01
Patent number
US06673850B1

Reaction notes

Loading…