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

HRID 860637Notes

Reaction equation

HRID 860637 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 nuetralized with 1N HCl (7.23 mL) and diluted with ethyl acetate (150 mL). The two phases are seperated 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 seperated
  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-42a2e821e53c4fbb8bf6b07bd470fe32
Source dataset
uspto-grants-2006_12
Patent number
US07153878B2

Reaction notes

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