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

HRID 1816196
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1816196
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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

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

Produkt 1

HCID 11960268methyl (S)-4-bromo-3-hydroxybutyrateAusbeute 74,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 107526
(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal
Katalysator
HCID 180AcetoneLösungsmittel
HCID 1061PhosphateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-00cd7f355490494493b461e627d20790
Quelldatensatz
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06884607B2

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