Hydrochloric Acid → 3-(4-Mercapto-2-methyl-phenyl)-propionic Acid Methyl Ester

HRID 854532Notes

Reaction equation

HRID 854532 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]C(=O)N(C)C)=[CH:8][C:7]=1[CH3:18].C[O-].[Na+].Cl>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:19])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([SH:12])=[CH:8][C:7]=1[CH3:18]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 574319693-(4-Dimethylcarbamoylsulfanyl-2-methyl-phenyl)-propionic acid methyl ester

Product 1

HCID 541446143-(4-Mercapto-2-methyl-phenyl)-propionic Acid Methyl EsterYield 118.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(4-Dimethylcarbamoylsulfanyl-2-methyl-phenyl)-propionic acid methyl ester (5.01 g, 17.8 mmol) is diluted with methanol (30 mL) and to this is added sodium methoxide (1.7 mL of 4M in methanol, 7.23 mmol). The reaction is heated to reflux under nitrogen and monitored by TLC. After complete conversion, 20 h., the reaction is allowed to cool to room temperature. The reaction is neutralized with 1N HCl (7.23 mL) and diluted with ethyl acetate (150 mL). The two phases are separated and the organic layer is washed with water (75 mL), then brine (75 mL). The organic layer is then dried over anhydrous sodium sulfate, then concentrated to yield 4.43 g crude product that is used without further purification.

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux under nitrogen
  3. customAfter complete conversion, 20 h.
  4. customThe two phases are separated
  5. washthe organic layer is washed with water (75 mL)
  6. dry with materialThe organic layer is then dried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4c93d052e1f249bdb61b21e7492c312b
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Reaction notes

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