Methyl iodide → (2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-(3-methoxycarbonylphenylthio)acetamide

HRID 545112Notes

Reaction equation

HRID 545112 reaction equation
[SH:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].Cl.[Cl:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:16][N:17]1[CH2:22][CH2:21][O:20][C@@H:19]([CH2:23][NH:24][C:25](=[O:28])[CH2:26]Cl)[CH2:18]1.[C:33](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O.O>[Cl:12][C:13]1[CH:14]=[C:15]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:16][N:17]1[CH2:22][CH2:21][O:20][C@@H:19]([CH2:23][NH:24][C:25](=[O:28])[CH2:26][S:1][C:2]2[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O:7][CH3:33])=[O:6])[CH:3]=2)[CH2:18]1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 95737Benzoic acid, 3-mercapto-HCID 67169608(2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}chloroacetamide hydrochloride

Product 1

HCID 67170774(2S)-N-{[4-(3,4-dichlorobenzyl)morpholin-2-yl]methyl}-(3-methoxycarbonylphenylthio)acetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-mercaptobenzoic acid (840 mg) and the resultant product (2.1 g) of (1-2) were dissolved in dimethylformamide (50 mL), potassium carbonate (2.1 g) was added, and the mixture was stirred at room temperature for 4 hrs. Methyl iodide (0.34 mL) was added, and the mixture was further stirred for 1 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography using a mixed solvent of chloroform and methanol as an eluent. The solvent was evaporated from the eluent to give the title compound (2.0 g) as a white amorphous solid.

Workup

  1. stirringthe mixture was further stirred for 1 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography
  7. customThe solvent was evaporated from the eluent

Sources & evidence

ORD record
ord-722f5a1afad949b3a88e168036c79dae
Source dataset
uspto-grants-2011_05
Patent number
US07935700B2

Reaction notes

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