Phosphate → HCID 12068238, compound

HRID 2187248Notes

Reaction equation

HRID 2187248 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, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
40 °C

Procedure

As the present enzyme, each of the various commercial enzymes shown in Table 1 was added in an amount shown in Table 2 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 2 elapsed, an aliquot of the reaction solution was removed and analyzed by HPLC [column: Sumichiral OA-5000, 4.6 mmφ×15 cm (Shumika Bunseki Center)], and the optical purity and reaction yield of the formed 2-oxobicyclo [3.1.0]hexane-6-carboxylic acid were determined. (−)-(1R,5S,6R)-2-oxobicyclo [3.1.0]hexane6-carboxylic acid was obtained in excess. The results are shown in Table 2.

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-5a7d426a8fc3457dbc0bfd23894a6a38
Source dataset
uspto-grants-2002_06
Patent number
US06407284B1

Reaction notes

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