Hydrochloric Acid → 3,3,3-Trifluoro-2-hydroxy-2-methylpropanenitrile
Reaction equation
FC(F)(F)[C@](O)(C)C(O)=O.[F:11][C:12]([F:19])([F:18])[C@:13]([OH:17])([CH3:16])[C:14]#[N:15].FC(F)(F)C(C)=O.[C-]#N.[Na+].Cl>>[F:11][C:12]([F:19])([F:18])[C:13]([OH:17])([CH3:16])[C:14]#[N:15]Participants
Procedure
In a preferred embodiment, (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid is prepared by reaction of (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropanenitrile with acid. (S)-3,3,3-Trifluoro-2-hydroxy-2-methylpropanenitrile can be prepared by reacting 1,1,1-trifluoroacetone with sodium cyanide in the presence of hydrochloric acid to form racemic 3,3,3-trifluoro-2-hydroxy-2-methylpropanenitrile. The racemic 3,3,3-trifluoro-2-hydroxy-2-methylpropanenitrile is then reacted with an acid chloride such as butyryl chloride to form the ester. The racemic ester is reacted with a lipase enzyme such as crude porcine pancreatic lipase that selectively cleaves the ester group from the (R) enantiomer leaving the ester of the (S) enantiomer. The ester group of the (S) enantiomer is then removed using standard procedures to provide (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropanenitrile, which is in turn treated with acid such as sulfuric acid or hydrochloric acid to form (S)-3,3,3-trifluoro-2-hydroxy-2-methylpropanoic acid.
Sources & evidence
- ORD record
- ord-2c38100d2875413184b3600bff689189
- Source dataset
- uspto-grants-2000_08
- Patent number
- US06110729
Reaction notes
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