Reaction #806254

Reaction equation

ethyl (S)-4-chloro3-hydroxybutyrate

NaCN

→

ethyl (R)-4-cyano-3-hydroxybutyrate

Solvents

potassium phosphate

Conditions

Workup

1. 1
   WashAfter fifty seven hours the mixture was washed with ethyl acetate (2 times 250 mL)
2. 2
   Dryingthe combined organics dried over anhydrous sodium sulfate
3. 3
   FiltrationThe mixture was filtered
4. 4
   Otherevaporated on a rotary evaporator

Procedure

To a well stirred solution of ethyl (S)-4-chloro3-hydroxybutyrate (8.25 g, 50 mmoles) in 300 mM potassium phosphate buffer, 300 mM NaCN pH 8.0 (1 L) at 30° C. was added halohydrin dehalogenase SEQ ID NO: 14 (9 g) as a lyophilized powder. After fifty seven hours the mixture was washed with ethyl acetate (2 times 250 mL) and the combined organics dried over anhydrous sodium sulfate. The mixture was filtered and evaporated on a rotary evaporator to give essentially pure ethyl (R)-4-cyano-3-hydroxybutyrate, as determined using the gas chromatography method and elution time data described in Example 6, hereinbelow.

Source