Trimethylsilyl iodide → N-(3-Acetylthio-2-methylpropanoyl)-N-cyclobutylglycine
Reaction equation
C([O:5][C:6](=[O:22])[CH2:7][N:8]([C:13](=[O:21])[CH:14]([CH3:20])[CH2:15][S:16][C:17](=[O:19])[CH3:18])[CH:9]1[CH2:12][CH2:11][CH2:10]1)(C)(C)C.C[Si](I)(C)C>C(Cl)Cl>[C:17]([S:16][CH2:15][CH:14]([CH3:20])[C:13]([N:8]([CH:9]1[CH2:10][CH2:11][CH2:12]1)[CH2:7][C:6]([OH:22])=[O:5])=[O:21])(=[O:19])[CH3:18]Participants
Procedure
To a stirred, argon flushed solution of N-(3-acetylthio-2-methyl-propanoyl)-N-cyclobutylglycine t-butyl ester (28.4 g, 0.086 mol) in methylene chloride was added trimethylsilyl iodide (18.0 g, 0.09 mol). After stirring at room temperature for 40 minutes the reaction was quenched by the addition of 50 ml of water. To this mixture, after stirring for 1 hour, was added 150 ml of 4% aqueous HCl, and the mixture was extracted with methylene chloride. The organic extracts were combined, dried over MgSO4, and evaporated to yield 21.9 g (90%) of the desired product as a light brown oil. This compound was characterized as its DCHA salt, prepared by adding DCHA to an ethereal solution of the compound until bringing the solution to pH 9. The salt was collected and recrystallized in acetonitrile to yield a white crystalline solid, m.p. 162.5°-164.5° C.
Workup
- customwas quenched by the addition of 50 ml of water
- stirringTo this mixture, after stirring for 1 hour
- additionwas added 150 ml of 4% aqueous HCl
- extractionthe mixture was extracted with methylene chloride
- dry with materialdried over MgSO4
- customevaporated
Sources & evidence
- ORD record
- ord-827e344eef0d4194928f382c29c53e69
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04256761
Reaction notes
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