Water → 2-Ethyl thiazolidine-2-carboxylic acid methyl ester

HRID 903888

Reaction equation

HRID 903888 reaction equation
[CH2:1]([C:3]1([C:8]([OH:10])=[O:9])[NH:7][CH2:6][CH2:5][S:4]1)[CH3:2].O.[C:12](=O)(O)[O-].[Na+]>Cl.CO>[CH3:12][O:9][C:8]([C:3]1([CH2:1][CH3:2])[NH:7][CH2:6][CH2:5][S:4]1)=[O:10]

Participants

5

Reactant 3

HCID 962WaterHCID 198462Thiazolidinecarboxylic acid, 2-ethyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 217820732-Ethyl thiazolidine-2-carboxylic acid methyl esterYield 18.4%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

10.0 g of the 2-ethyl-thiazolidine-2-carboxylic acid thus obtained was dissolved in 200 ml of 20% hydrogen chloride-methanol solution. After being refluxed for 30 minutes, the reaction mixture was concentrated under reduced pressure to afford a residue, to which was added water, and was then neutralized with an aqueous saturated solution of sodium bicarbonate. Upon extracting with ethyl acetate, the extract was chromatographed on a column of silica gel to give 2.0 g (yield 18.4%) of 2-ethyl-thiazolidine-2-carboxylic acid methyl ester with a reflex index of nD26 1.501.

Workup

  1. temperatureAfter being refluxed for 30 minutes
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto afford a residue
  4. extractionUpon extracting with ethyl acetate
  5. customthe extract was chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-49855af150524eecbe110a1c074cd2b8
Source dataset
uspto-grants-1980_10
Patent number
US04229461

Linked notes

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