4-Chlorostyrene oxide → (S)-2-(4-Chlorophenyl)oxirane

HRID 641122Notes

Reaction equation

HRID 641122 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]2[O:8][CH2:7]2)=[CH:4][CH:3]=1.N([O-])=O.[Na+]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C@@H:6]2[O:8][CH2:7]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 1970104-Chlorostyrene oxideHCID 23668193Sodium Nitrite

Product 1

HCID 11105582(S)-2-(4-Chlorophenyl)oxirane

Procedure

To 20 ml of Tris-SO4 buffer (50 mM, pH=7.3) containing 2 mM of para-chlorostyrene oxide and 1.2 mM of NaNO2, 1.0 mg of purified enzyme, obtained as described in Example 1, was added. At 58% conversion, reaction was stopped and the solution was extracted with diethylether. The organic phase was analysed by chiral GC. The remaining (S)-para-chloro styrene oxide was obtained with an e.e. of higher than 99%.

Workup

  1. customobtained
  2. additionwas added
  3. customAt 58% conversion, reaction
  4. extractionthe solution was extracted with diethylether

Sources & evidence

ORD record
ord-c5b315dee73f469082903b0970744ce1
Source dataset
uspto-grants-2010_04
Patent number
US07695942B2

Reaction notes

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