4-Thiazolidinecarboxylic acid, 2-ethyl- → HCID 21162278, compound

HRID 1701310Notes

Reaction equation

HRID 1701310 reaction equation
[C:1]([S:4][CH2:5][CH:6]([CH3:10])[C:7](Cl)=[O:8])(=[O:3])[CH3:2].[CH2:11]([CH:13]1[NH:17][CH:16]([C:18]([OH:20])=[O:19])[CH2:15][S:14]1)[CH3:12]>[OH-].[Na+]>[C:1]([S:4][CH2:5][CH:6]([CH3:10])[C:7]([N:17]1[CH:16]([C:18]([OH:20])=[O:19])[CH2:15][S:14][CH:13]1[CH2:11][CH3:12])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 983444-Thiazolidinecarboxylic acid, 2-ethyl-HCID 103458Ethanethioic acid, S-(3-chloro-2-methyl-3-oxopropyl) ester

Product 1

HCID 21162278HCID 21162278, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

3-Acetylthio-2-methylpropanoic acid chloride (5.4 g. prepared from 3-acetylthio-2-methylpropanoic acid and thionyl chloride, b.p. 80°) and 2 N sodium hydroxide (15 ml.) are added to a solution of 2-ethyl-4-thiazolidinecarboxylic acid [Z.Naturforschg, 17b, 765 (1962)] (5.2 g.) in normal sodium hydroxide (30 ml.) chilled in an ice-water bath. After three hours stirring at room temperature, the mixture is extracted with ether, the aqueous phase is acidified and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and concentrated to dryness in vacuo to yield 3-(3-acetylthio-2-methylpropanoyl)-2-ethyl-4-thiazolidinecarboxylic acid.

Workup

  1. temperaturechilled in an ice-water bath
  2. extractionthe mixture is extracted with ether
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over magnesium sulfate
  5. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-efb3924c67104a5d950f0a892919884c
Source dataset
uspto-grants-1980_03
Patent number
US04192878

Reaction notes

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