Phosphate → HCID 11149663, compound

HRID 2187249Notes

Reaction equation

HRID 2187249 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 11149663HCID 11149663, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
40 °C

Procedure

Each of the various commercial enzymes shown in Table 3 was added in an amount shown in Table 4 to 1 ml of 100 mM phosphate buffer (pH 7.0) and dissolved therein. 10 mg of racemic ethyl(1SR,5RS,6SR)-2-oxobicyclo [3.1.0]hexane-6-carboxylate was dissolved in 1 ml n-hexane, then added to the enzyme solution, and heated to 40° C. and the mixture was stirred. After the time shown as the reaction time in Table 4 elapsed, an aliquot of the reaction solution was removed and analyzed in the same manner as in Examples 1 to 8 to determine the optical purity and reaction yield of the formed 2-oxobicyclo[3.1.0]hexane-6-carboxylic acid. (+)-(1S,5R, 6S)-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid was obtained in excess. The results are shown in Table 4.

Workup

  1. additionwas added in an amount
  2. dissolutiondissolved
  3. additionadded to the enzyme solution
  4. customan aliquot of the reaction solution was removed
  5. customthe optical purity and reaction yield of the formed 2-oxobicyclo[3.1.0]hexane-6-carboxylic acid

Sources & evidence

ORD record
ord-437238245ac34dc2b52c95958ec5b6bc
Source dataset
uspto-grants-2002_06
Patent number
US06407284B1

Reaction notes

Loading…