NADP nicotinamide-adenine-dinucleotide phosphate → (R)-2-Chloro-1-(3-chlorophenyl)ethanol

HRID 1678040Notes

Reaction equation

HRID 1678040 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+]>C1(C)C=CC=CC=1>[Cl:61][CH2:62][C@@H:63]([C:65]1[CH:70]=[CH:69][CH:68]=[C:67]([Cl:71])[CH:66]=1)[OH:64]

Participants

6

Reactant 4

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

Product 1

HCID 10375278(R)-2-Chloro-1-(3-chlorophenyl)ethanolYield 90.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
30 °C

Procedure

To 50 ml of a culture solution of E. coli HB101 (pNTCMG1) prepared in the same manner as in Example 6, 5 g of glucose, 6 mg of NADP, 4 g of 2-chloro-1-(3′-chlorophenyl)ethanone and 4 g of toluene were added. The mixture was stirred at 30° C. for 24 hours while adjusting the pH of the mixture to 6.5 by adding 5 M sodium hydroxide dropwise. After completion of the reaction, the reaction solution was extracted with toluene. The solvent was removed and then an extracted material was analyzed. As a result, (R)-2-chloro-1-(3′-chlorophenyl)ethanol having an optical purity of 82.0% e.e. was obtained in a yield of 90.5%.

Workup

  1. additionwere added
  2. customAfter completion of the reaction
  3. extractionthe reaction solution was extracted with toluene
  4. customThe solvent was removed

Sources & evidence

ORD record
ord-2aa0bfe703fb4c8ebdd2b96752c624e7
Source dataset
uspto-grants-2011_08
Patent number
US08008461B2

Reaction notes

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