Hydrochloric Acid → 3,3,3-Trifluoro-2-hydroxy-2-methylpropanenitrile
反応式
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]参加物
実験手順
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.
出典と根拠
- ORDレコード
- ord-2c38100d2875413184b3600bff689189
- 出典データセット
- uspto-grants-2000_08
- 特許番号
- US06110729
反応ノート
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