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

HRID 1702203Notes

Reaction equation

HRID 1702203 reaction equation
[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]([O:9]C(C)(C)C)=[O:8])[N:4]([C:14](=[O:22])[C@H:15]([CH3:21])[CH2:16][S:17][C:18](=[O:20])[CH3:19])[C:3]1=[O:23].FC(F)(F)C(O)=O>>[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]([OH:9])=[O:8])[N:4]([C:14](=[O:22])[C@H:15]([CH3:21])[CH2:16][S:17][C:18](=[O:20])[CH3:19])[C:3]1=[O:23]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 13053996tert.-butyl (4S)-1-methyl-3-[(2S)-3-acetylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate

Product 1

HCID 13053994(4S)-1-methyl-3-[(2S)-3-acetylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylic acidYield 99.5%

Procedure

A mixture of 0.72 g of tert.-butyl (4S)-1-methyl-3-[(2S)-3-acetylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylate and 3.5 ml of trifluoroacetic acid is stirred at room temperature for one hour. Then, the reaction mixture is treated in the same manner as described in Example 1-(5). 0.6 g of (4S)-1-methyl-3-[(2S)-3-acetylthio-2-methylpropionyl]-2-oxo-imidazolidine-4-carboxylic acid is obtained as colorless syrup. Yield: quantitative.

Workup

  1. additionThen, the reaction mixture is treated in the same manner

Sources & evidence

ORD record
ord-db923aa977e74b47b300356e9a85ab93
Source dataset
uspto-grants-1983_04
Patent number
US04380644

Reaction notes

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