Sodium Hydroxide → HCID 15512455, compound

HRID 1058113Notes

Reaction equation

HRID 1058113 reaction equation
[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]([O:5][CH2:6][C:7](=[O:14])[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:4].O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.[OH-].[Na+]>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>[CH3:1][C:2]([CH3:16])([CH3:15])[C:3]([O:5][CH2:6][C@H:7]([OH:14])[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 155124522-Oxo-2-pyridin-3-ylethyl 2,2-dimethylpropanoate

Product 1

HCID 15512455HCID 15512455, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 5886NADP nicotinamide-adenine-dinucleotide phosphateCatalyst

Procedure

2-Oxo-2-pyridin-3-ylethyl 2,2-dimethylpropanoate (2 g), 2.8 g of glucose, 2.3 mg of NADP and 0.02 ml of Triton X×100 were added to 20 ml of the same culture fluid as used in Example 11, and the reaction was carried at 30° C. with stirring for 2 hours while adjusting the pH to 6.5 with a 5 N aqueous sodium hydroxide solution. After completion of the reaction, the reaction mixture was extracted with ethyl acetate, and the 30 extract was concentrated under reduced pressure to give 2.1 g of (R)-2-hydroxy-2-pyridin-3-ylethyl 2,2-dimethylpropanoate as a light-yellow oil. The optical purity was determined by the same method as used in EXAMPLE 10 and was 100% ee.

Workup

  1. customwas carried at 30° C.
  2. customAfter completion of the reaction
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. extractionthe 30 extract
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-d4e1b08e8efa44889fdbbe7de384d95f
Source dataset
uspto-grants-2003_02
Patent number
US06515134B1

Reaction notes

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