Nadide (JAN/USAN/INN) → (+)-2,2,2-Trifluoro-1-phenylethanol

HRID 346436

Reaction equation

HRID 346436 reaction equation
P([O-])(O)(O)=O.[K+].P([O-])([O-])(O)=O.[K+].[K+].C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[F:70][C:71]([F:81])([F:80])[C:72]([C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1)=[O:73].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.C(OCC)(=O)C>[F:70][C:71]([F:80])([F:81])[C@H:72]([C:74]1[CH:79]=[CH:78][CH:77]=[CH:76][CH:75]=1)[OH:73]

Participants

8

Reactant 5

HCID 5893Nadide (JAN/USAN/INN)HCID 99052,2,2-TrifluoroacetophenoneHCID 10340Sodium CarbonateHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 21889592Monopotassium phosphate dipotassium phosphate

Product 1

HCID 1472401(+)-2,2,2-Trifluoro-1-phenylethanol

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 20 ml of 50 mM potassium dihydrogenphosphate-dipotassium hydrogenphosphate buffer (pH 7.0) are added 1 g of the washed bacterial bodies prepared in Example 7, 12 mg of NAD+ and 2.5 g of glucose. After adding 240 mg of 2,2,2-trifluoroacetophenone to this mixture, the pH of this mixture is adjusted to 7.0 with a 15% aqueous sodium carbonate solution. The reaction is executed by stirring thus obtained mixture (reaction mixture) at 30° C. for 4 hours. After completion of the reaction, 25 ml of ethyl acetate is poured into the reaction mixture and stirred, followed by centrifugal separation for separately collecting the organic phase and the aqueous phase. To the collected aqueous phase is added 25 ml of ethyl acetate again, and the similar operation is repeated. After concentrating the combined organic phase obtained in such a manner, the concentrate is dissolved in 30 ml of chloroform and dried using anhydrous Na2SO4. After drying, chloroform is distilled off to obtain (S)-2,2,2-trifluoro-1-phenylethanol.

Workup

  1. custommixture (reaction mixture) at 30° C. for 4 hours
  2. additionis poured into the reaction mixture
  3. stirringstirred
  4. customfollowed by centrifugal separation
  5. customfor separately collecting the organic phase
  6. additionTo the collected aqueous phase is added 25 ml of ethyl acetate again
  7. concentrationAfter concentrating the combined organic phase
  8. customobtained in such a manner
  9. customdried
  10. customAfter drying
  11. distillationchloroform is distilled off

Sources & evidence

ORD record
ord-4b0cf4e649aa43c9a11c3910c3fc2d2b
Source dataset
uspto-grants-2007_02
Patent number
US07172894B2

Linked notes

Loading…