Trifluoroacetic acid → (4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylic acid

HRID 1702201Notes

Reaction equation

HRID 1702201 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[CH2:13][C@@H:12]([C:14]([O:16]C(C)(C)C)=[O:15])[N:11]([C:21](=[O:34])[C@H:22]([CH3:33])[CH2:23][S:24][C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:10]1=[O:35]>C1(C)C=CC=CC=1>[CH3:8][N:9]1[CH2:13][C@@H:12]([C:14]([OH:16])=[O:15])[N:11]([C:21](=[O:34])[C@H:22]([CH3:33])[CH2:23][S:24][C:25](=[O:32])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:10]1=[O:35]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 13053985tert-butyl (4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Product 1

HCID 13053988(4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylic acidYield 92.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

15 ml of trifluoroacetic acid are added to 4.0 g of tert.-butyl (4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate, and the mixture is stirred at room temperature for 2 hours. The reaction mixture is condensed under reduced pressure. Toluene is added to the residue, and said mixture is again condensed under reduced pressure. The residue thus obtained is recrystallized from a mixture of ethyl acetate and n-hexane. 3.2 g of (4S)-1-methyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylic acid is thereby obtained as colorless syrup. The physico-chemical properties of this product are identical with those of the sample obtained in Example 1-(5).

Workup

  1. customcondensed under reduced pressure
  2. customcondensed under reduced pressure
  3. customThe residue thus obtained
  4. customis recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-0c05b4f8e105465f94f3b84b5858ee26
Source dataset
uspto-grants-1983_04
Patent number
US04380644

Reaction notes

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