Methanol → (3-Methyl-4-methylsulfanyl-phenyl)-acetic acid methyl ester

HRID 546154Notes

Reaction equation

HRID 546154 reaction equation
C(OC(=O)NC1C=CC=C(CN2C=CC(N[C:21](=[O:40])[C@@H:22]([C:29]3[CH:34]=[CH:33][C:32]([S:35]([CH3:38])(=O)=O)=[C:31](Cl)[CH:30]=3)CC3CCCC3)=N2)C=1)(C)(C)C.[CH3:42][OH:43].[CH:44](Cl)(Cl)Cl>S(=O)(=O)(O)O>[CH3:42][O:43][C:21](=[O:40])[CH2:22][C:29]1[CH:34]=[CH:33][C:32]([S:35][CH3:38])=[C:31]([CH3:44])[CH:30]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6212ChloroformHCID 67190452HCID 67190452, compound

Product 1

HCID 67193242(3-Methyl-4-methylsulfanyl-phenyl)-acetic acid methyl esterYield 83%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
70 °C

Procedure

(3-Methyl-4-methylsulfanyl-phenyl)-acetic acid (prepared as in PCT WO 2004/052869 A1, Example 57, 1.50 g, 7.64 mmol) was placed in a pressure bottle with methanol (15 mL) and concentrated sulfuric acid (9 drops) and heated at 70° C. for 16 h and then stirred at 25° C. for 2 days. The reaction was then diluted with chloroform and concentrated with silica gel (4 g) in vacuo and purified on Biotage Flash chromatography system (40M column, silica gel, 20% ethyl acetate/hexanes) to afford (3-methyl-4-methylsulfanyl-phenyl)-acetic acid methyl ester (1.34 g, 83%) as an amber oil.

Workup

  1. concentrationconcentrated with silica gel (4 g) in vacuo
  2. custompurified on Biotage Flash chromatography system (40M column, silica gel, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-bc319c4b1482434d92699619b32e2eec
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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