Sodium Cyanide → HCID 87425379, compound

Participants

Reaction Conditions

Reaction Steps

200 mg (1.53 mmol) of racemic methyl 2-methyloxiraneacetate was dissolved in 30 mL Tris-SO4 buffer (200 mM, pH 7.5), followed by addition of purified enzyme (15 mg of halohydrin dehalogenase HheC in 450 ρL buffer) and 38 mg (0.77 mmol) NaCN. The reaction mixture was stirred at room temperature (22° C.) and monitored by gas chromatography (GC). The reaction was stopped after 2 h and extracted 3×25 mL ethylacetate. The organic phase was dried over Na2SO4 and evaporated. The crude product was chromatographed on a silica gel 60 H column using pentane/CH2Cl2 (4:6) as eluent. This yielded pure (S)-methyl 2-methyloxiraneacetate (75 mg, 37% yield, e.e. 81%) and (S)-methyl 4-cyano-3-hydroxy-3-methylbutanoate (84 mg, 35% yield, e.e.>99%). The optical purities were determined by GC using a Chiraldex G-TA column (30 m×0.25 mm×0.25 μm). The NMR data were identical with those of synthesized racemic reference compounds.

Provenance & Evidence