Methanol → HCID 67147820, compound

HRID 1864578Notes

Reaction equation

HRID 1864578 reaction equation
[CH2:1]([O:3][C@@H:4]([CH2:8][C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH3:22])[CH:16]=2)=[CH:13][CH:14]=1)[C:5]([OH:7])=[O:6])[CH3:2].[CH3:23]O>S(=O)(=O)(O)O>[CH2:1]([O:3][C@@H:4]([CH2:8][C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([NH:21][CH3:22])[CH:16]=2)=[CH:13][CH:14]=1)[C:5]([O:7][CH3:23])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 887MethanolHCID 67148178HCID 67148178, compound

Product 1

HCID 67147820HCID 67147820, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidCatalyst

Conditions

Temperature
65 °C

Procedure

0.1 g (0.3 mmol) of 2(S)-ethoxy-3-[6-(3-methylaminophenyl)pyrid-3-yl]propanoic acid is placed in 5 ml of methanol and 2 drops of concentrated sulfuric acid are added. The reaction medium is heated at 65° C. for 18 hours. The methanol is evaporated off and the residue is taken up in an ethyl acetate/water mixture. The pH is brought to 7 by addition of 1N sodium hydroxide solution and the reaction medium is extracted with ethyl acetate. The ethyl acetate phase is dried over sodium sulfate, filtered and evaporated. 70 mg (70%) of methyl 2(S)-ethoxy-3-[6-(3-methylaminophenyl)pyrid-3-yl]propanoate are obtained.

Workup

  1. customThe methanol is evaporated off
  2. additionThe pH is brought to 7 by addition of 1N sodium hydroxide solution
  3. extractionthe reaction medium is extracted with ethyl acetate
  4. dry with materialThe ethyl acetate phase is dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-556ec6126e654b92a6a3fe153fa36057
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

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