Phosphate → HCID 12068238, compound

HRID 2187250Notes

Reaction equation

HRID 2187250 reaction equation
P([O-])([O-])([O-])=O.[O:6]=[C:7]1[CH2:12][CH2:11][CH:10]2[CH:8]1[CH:9]2[C:13]([O:15]CC)=[O:14]>CCCCCC>[O:6]=[C:7]1[CH2:12][CH2:11][C@H:10]2[C@@H:8]1[C@@H:9]2[C:13]([OH:15])=[O:14]

Participants

4

Reactant 2

HCID 1061PhosphateHCID 565357Ethyl 2-oxobicyclo[3.1.0]hexane-6-carboxylate

Product 1

HCID 12068238HCID 12068238, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
40 °C

Procedure

2.0 mg of the crude enzyme powder of the present enzyme obtained in Reference Example 14 from Burkholderia cepacia SC-20 was added to, and suspended in, 1 ml of 100 mM phosphate buffer (pH 7.0). 10 mg of racemic ethyl(1SR,5RS,6SR)-2-oxobicyclo[3.1.0]hexane-6-carboxylate was dissolved in 1 ml n-hexane, added to the enzyme solution, and heated to 40° C., and the mixture was stirred. After 13 hours, an aliquot of the reaction solution was removed and analyzed in the same manner as in Examples 1 to 8, and the formed 2-oxobicyclo[3.1.0]hexane-6-carboxylic acid was measured for optical purity and reaction yield. As a result, (+)-(1R,5S,6R)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid was obtained with 62.9% optical purity in 14.8% yield.

Workup

  1. custom2.0 mg of the crude enzyme powder of the present enzyme obtained in Reference Example 14 from Burkholderia cepacia SC-20
  2. additionwas added to, and
  3. additionadded to the enzyme solution
  4. customan aliquot of the reaction solution was removed
  5. customthe formed 2-oxobicyclo[3.1.0]hexane-6-carboxylic acid was measured for optical purity and reaction
  6. customyield

Sources & evidence

ORD record
ord-ddf0e6b845074a4489431207c66f9eec
Source dataset
uspto-grants-2002_06
Patent number
US06407284B1

Reaction notes

Loading…