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

HRID 355645노트

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HRID 355645 반응식
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]

참가 물질

9

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5b74250b968e454a91669c063b9877ef
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834261

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