Sodium Cyanide → HCID 87425379, compound

HRID 217575Notes

Reaction equation

HRID 217575 reaction equation
[CH3:1][C:2]1([CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:4][O:3]1.[C-:10]#[N:11].[Na+]>>[CH3:1][C@:2]1([CH2:5][C:6]([O:8][CH3:9])=[O:7])[CH2:4][O:3]1.[C:10]([CH2:4][C@@:2]([OH:3])([CH3:1])[CH2:5][C:6]([O:8][CH3:9])=[O:7])#[N:11]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 534272HCID 534272, compound

Product 2

HCID 87425379HCID 87425379, compoundYield 37%HCID 87425468HCID 87425468, compoundYield 35%

Conditions

Temperature
22 °C

Procedure

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.

Workup

  1. extractionextracted 3×25 mL ethylacetate
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. customThe crude product was chromatographed on a silica gel 60 H column

Sources & evidence

ORD record
ord-c6dbfc8382c24f5980fa3a93d26a08ac
Source dataset
uspto-grants-2012_06
Patent number
US08198069B2

Reaction notes

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