Sodium Carbonate → methyl (S)-4-bromo-3-hydroxybutyrate

HRID 1816196Notes

Reaction equation

HRID 1816196 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.C(OCCCC)(=O)C.[Br:21][CH2:22][C:23](=[O:29])[CH2:24][C:25]([O:27][CH3:28])=[O:26].C(=O)([O-])[O-].[Na+].[Na+]>P([O-])([O-])([O-])=O.O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.CC(C)=O>[Br:21][CH2:22][C@@H:23]([OH:29])[CH2:24][C:25]([O:27][CH3:28])=[O:26]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 31272Butyl AcetateHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 295655Methyl 4-bromo-3-oxobutanoate

Product 1

HCID 11960268methyl (S)-4-bromo-3-hydroxybutyrateYield 74.9%

Reagents, catalysts & solvents 3

HCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalCatalystHCID 180AcetoneSolventHCID 1061PhosphateSolvent

Procedure

A solution was prepared by dissolving 75 g of glucose, 0.85 g of oxidized form of nicotine adenine dinucleotide phosphate, 0.11 g of glucose dehydrogenase (glucose amino 2; by Amano enzyme) in 1500 g of a phosphate buffer solution (pH 6.5) and 1300 g of butyl acetate and 37 g of methyl 4-bromo-3-oxobutanoate were added thereto, and then 150 g of the acetone-treated cells of Penicillium citrinum IFO 463described above were added to thereto under stirring. 15% aqueous sodium carbonate solution was dropwise added thereto so that the pH of the reaction solution is maintained within a range of from 6.5±0.5. After stirring for 24 hours, 90 g of celite were added thereto and filtered under reduced pressure. The organic layer separated from the filtrate was concentrated under reduced pressure to give 28 g of methyl (S)-4-bromo-3-hydroxybutanoate, Chemical Purity: 88%, Optical purity: 97% e.e.

Workup

  1. customA solution was prepared
  2. additionabove were added to thereto
  3. temperatureso that the pH of the reaction solution is maintained within a range of from 6.5±0.5
  4. stirringAfter stirring for 24 hours
  5. addition90 g of celite were added
  6. filtrationfiltered under reduced pressure
  7. customThe organic layer separated from the filtrate
  8. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-00cd7f355490494493b461e627d20790
Source dataset
uspto-grants-2005_04
Patent number
US06884607B2

Reaction notes

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