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

HRID 1702211Notes

Reaction equation

[CH2:1]([N:5]1[CH2:9][C@@H:8]([C:10]([O:12]C(C)(C)C)=[O:11])[N:7]([C:17](=[O:30])[C@H:18]([CH3:29])[CH2:19][S:20][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:6]1=[O:31])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>>[CH2:1]([N:5]1[CH2:9][C@@H:8]([C:10]([OH:12])=[O:11])[N:7]([C:17](=[O:30])[C@H:18]([CH3:29])[CH2:19][S:20][C:21](=[O:28])[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:6]1=[O:31])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 56633050tert.-butyl (4S)-1-n-butyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Product 1

HCID 13054003(4S)-1-n-butyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylic acidYield 91.4%

Procedure

3.5 g of tert.-butyl (4S)-1-n-butyl-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). 2.8 g of (4S)-1-n-butyl-3-[(2S)-3-benzoylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylic acid are obtained as colorless crystals. Yield: 91.4% The physicochemical properties of this product are identical with those of the sample obtained in Example 6-(4).

Sources & evidence

ORD record: ord-38a0af1ed6ad42ba8bd3c03fd5db9ec7
Source dataset: uspto-grants-1983_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04380644

Reaction notes

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