NADP nicotinamide-adenine-dinucleotide phosphate → Ethyl (3S)-4-chloro-3-hydroxybutanoate

HRID 1678041Notes

Reaction equation

HRID 1678041 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.[OH-].[Na+].[Cl:63][CH2:64][C:65](=[O:72])[CH2:66][C:67]([O:69][CH2:70][CH3:71])=[O:68]>>[Cl:63][CH2:64][C@@H:65]([OH:72])[CH2:66][C:67]([O:69][CH2:70][CH3:71])=[O:68]

Participants

5

Reactant 4

HCID 5886NADP nicotinamide-adenine-dinucleotide phosphateHCID 14798Sodium HydroxideHCID 69484Ethyl 4-chloroacetoacetateHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Product 1

HCID 7019277Ethyl (3S)-4-chloro-3-hydroxybutanoateYield 93.1%

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, 6 g of glucose, 4 mg of NADP were added. The reaction solution was stirred at 30° C. While the pH of the reaction solution was adjusted to pH 6.5 by adding 5 M sodium hydroxide dropwise, 5 g in total of ethyl 4-chloro-3-oxobutyrate was added at a rate of 0.5 g/hour. Stirring was continued for a further 5 hours. After completion of the reaction, the reaction solution was extracted with ethyl acetate. The solvent was removed and then an extracted material was analyzed. As a result, ethyl (S)-4-chloro-3-hydroxybutyrate having an optical purity of 80.5% e.e. was obtained in a yield of 93.1%.

Workup

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

Sources & evidence

ORD record
ord-86b9b2de681b407483756a69aa8e6a36
Source dataset
uspto-grants-2011_08
Patent number
US08008461B2

Reaction notes

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