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

HRID 1702207Notes

Reaction equation

[CH2:1]([N:3]1[CH2:7][C@@H:6]([C:8]([O:10]C(C)(C)C)=[O:9])[N:5]([C:15](=[O:28])[C@H:16]([CH3:27])[CH2:17][S:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]1=[O:29])[CH3:2].FC(F)(F)C(O)=O>>[CH2:1]([N:3]1[CH2:7][C@@H:6]([C:8]([OH:10])=[O:9])[N:5]([C:15](=[O:28])[C@H:16]([CH3:27])[CH2:17][S:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:4]1=[O:29])[CH3:2]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 13054001tert.-butyl (4S)-1-ethyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Product 1

HCID 13053998(4S)-1-ethyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylic acidYield 95.2%

Procedure

4.0 g of tert.-butyl (4S)-1-ethyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate and 15 ml of trifluoroacetic acid are treated in the same manner as described in Example 2-(3). 3.3 g of (4S)-1-ethyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylic acid are obtained as colorless crystals. Yield: 95.2% The physico-chemical properties of this product are identical with those of the sample obtained in Example 4-(4).

Sources & evidence

ORD record: ord-4a22111b18064162babbf1782e029755
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04380644

Reaction notes

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