Potassium Chloride → (2S,3S)-2 ethyl-3-hydroxybutyramide

HRID 355645Notes

Reaction equation

HRID 355645 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.OP([O-])(O)=O.[K+].OP([O-])([O-])=O.[K+].[K+].[O-]S([O-])(=O)=O.[Mg+2].[Cl-].[K+].[CH2:34]([CH:36]([C:40](=[O:42])[CH3:41])[C:37]([NH2:39])=[O:38])[CH3:35].COC1C=CC(C=O)=CC=1>C(O)C>[CH2:34]([C@@H:36]([C@@H:40]([OH:42])[CH3:41])[C:37]([NH2:39])=[O:38])[CH3:35]

Participants

9

Reactant 7

HCID 4873Potassium ChlorideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 24450Potassium Phosphate, DibasicHCID 312444-MethoxybenzaldehydeHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 516951Monobasic potassium phosphateHCID 198158932-Ethylacetoacetamide

Product 1

HCID 11829477(2S,3S)-2 ethyl-3-hydroxybutyramideYield 49.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Geotrichum candidum (ATCC 34614) was cultured according to the method of Buisson and Azerad (Tet. Lett. 27, 2631-2634 (1986), herein incorporated by reference) in one liter of a medium of glucose (30 grams), KH2PO4 (1 gram), K2HPO4 (2 grams), corn steep liquor (10 grams) MgSO4.7H20 (0.5 gram), NaNO3 (2 grams), FeSO4.7H20 (0.02 gram), and KCl (0.5 gram) with rotary shaking at 25° C. Two grams of 2-ethyl-3-ketobutyramide was dissolved in 2 ml of 95% ethanol, the resulting solution was added to the culture, and shaking was resumed. The reaction was followed by TLC (staining with anisaldehyde) to monitor the consumption of starting material and the production of product alcohol. After 48-72 hours the reaction was judged complete, and the reaction was terminated by removing from the shaker and adding 20-30 grams of Celite. The resulting suspension was suction filtered through a pad of Celite and the clear yellow filtrate was extracted with ethyl acetate (4×200 ml). The extracts were combined, dried over MgSO4, filtered, and rotary evaporated to leave 1 gram of (2S,3S)-2 ethyl-3-hydroxybutyramide as a yellowish solid.

Workup

  1. additionthe resulting solution was added to the culture
  2. customthe consumption of starting material
  3. customthe reaction was terminated
  4. customby removing from the shaker
  5. additionadding 20-30 grams of Celite
  6. filtrationfiltered through a pad of Celite
  7. extractionthe clear yellow filtrate was extracted with ethyl acetate (4×200 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customrotary evaporated

Sources & evidence

ORD record
ord-5b74250b968e454a91669c063b9877ef
Source dataset
uspto-grants-1998_11
Patent number
US05834261

Reaction notes

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