NADP nicotinamide-adenine-dinucleotide phosphate → 2-Chloro-1-(3-chloro-phenyl)-ethanol

HRID 2055066Notes

Reaction equation

HRID 2055066 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C1C=[N+]([C@@H]2O[C@H](COP(OP(OC[C@H]3O[C@@H](N4C5N=CN=C(N)C=5N=C4)[C@H](OP(O)(O)=O)[C@@H]3O)(O)=O)(O)=O)[C@@H](O)[C@H]2O)C=C(C(N)=O)C=1.[Cl:61][CH2:62][C:63]([C:65]1[CH:70]=[CH:69][CH:68]=[C:67]([Cl:71])[CH:66]=1)=[O:64].[OH-].[Na+]>>[Cl:61][CH2:62][CH:63]([C:65]1[CH:70]=[CH:69][CH:68]=[C:67]([Cl:71])[CH:66]=1)[OH:64]

Participants

5

Reactant 4

HCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal2×HCID 168006Ethanone, 2-chloro-1-(3-chlorophenyl)-

Product 1

HCID 114695632-Chloro-1-(3-chloro-phenyl)-ethanolYield 96%

Conditions

Temperature
30 °C

Procedure

The culture of the recombinant Escherichia coli HB101(pNTRG) as obtained in Example 8 was subjected to ultrasonic cell disruption using SONIFIRE 250 (product of BRANSON). To 20 ml of this cell disruption fluid, there were added 2,000 U of glucose dehydrogenase (product of Amano Pharmaceutical Co., Ltd.), 3 g of glucose, 2 mg of NADP and 2 g of 2-chloro-1-(3′-chlorophenyl)ethanone. This reaction mixture was stirred at 30° C. for 18 hours while adjusting the pH to 6.5 by addition of 5 M sodium hydroxide. After completion of the reaction, this reaction mixture was extracted with toluene, the solvent was then removed, and the extract was analyzed. 2-Chloro-1-(3′-chlorophenyl)ethanol was obtained in 96% yield. The 2-chloro-1-(3′-chlorophenyl)ethanol formed on that occasion was the R form with an optical purity of 99.9% ee.

Workup

  1. customas obtained in Example 8
  2. customAfter completion of the reaction
  3. extractionthis reaction mixture was extracted with toluene
  4. customthe solvent was then removed

Sources & evidence

ORD record
ord-45f69e5a8d054a9cb895e773c9c6a685
Source dataset
uspto-grants-2008_02
Patent number
US07332312B2

Reaction notes

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