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

HRID 641119

反応式

HRID 641119 の反応式
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH:8]2[O:10][CH2:9]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[N-]=[N+]=[N-].[Na+]>>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C@@H:8]2[O:10][CH2:9]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

参加物

3

反応物 2

HCID 33557Sodium AzideHCID 922282-(4-Nitrophenyl)oxirane

生成物 1

HCID 1237169(S)-2-(4-Nitrophenyl)oxirane

実験手順

To 1 ml of Tris-SO4 buffer (50 mM, pH=7.3) containing 0.25 mM of para-nitro styrene oxide and 0.5 mM of NaN3, 0.7 mg of purified enzyme, obtained according to Example 1, was added. The reaction was stopped after 15 min and the solution was extracted with diethylether. The organic phase was analysed by chiral HPLC. The remaining (S)-para-nitro styrene oxide was obtained with an e.e. >99% and the product (R)-2-azido-1-(para-nitro-phenyl)-ethanol with an e.e. of 96%. The other regio-isomer 2-azido-2-(para-nitro-phenyl)-ethanol was formed in a ratio of 1:217 compared to (R)-2-azido-1-(para-nitro-phenyl)-ethanol. From this we concluded that the enzymatic azidolysis is almost absolutely regioselective (β selectivity>99%). The observed lower regioselectivity during a kinetic resolution on a longer time scale was due to the unwanted chemical side reaction.

後処理

  1. customobtained
  2. additionwas added
  3. extractionthe solution was extracted with diethylether

出典と根拠

ORDレコード
ord-3543a02835fd4116aaec630e3fec4569
出典データセット
uspto-grants-2010_04
特許番号
US07695942B2

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