Sodium Azide → (S)-2-(4-Chlorophenyl)oxirane

HRID 641121Notes

Reaction equation

HRID 641121 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-]=[N+]=[N-].[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 33557Sodium AzideHCID 1970104-Chlorostyrene oxide

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 NaN3, 1.0 mg of purified enzyme, obtained as described in Example 1, was added. At 55% 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% and (R)-2-azido-1-(para-chloro-phenyl)-ethanol with an e.e. of 98%.

Workup

  1. customobtained
  2. additionwas added
  3. customAt 55% conversion, reaction
  4. extractionthe solution was extracted with diethylether

Sources & evidence

ORD record
ord-653571a75d614f61b955759e79c948ce
Source dataset
uspto-grants-2010_04
Patent number
US07695942B2

Reaction notes

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