Ethyl Acetoacetate → ethyl (3R)-3-hydroxybutanoate

HRID 355644노트

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HRID 355644 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].[C:32]([O:38][CH2:39][CH3:40])(=[O:37])[CH2:33][C:34]([CH3:36])=[O:35].COC1C=CC(C=O)=CC=1>C(O)C>[OH:35][C@H:34]([CH3:36])[CH2:33][C:32]([O:38][CH2:39][CH3:40])=[O:37]

참가 물질

8

반응물 6

HCID 8868Ethyl AcetoacetateHCID 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 phosphate

생성물 1

HCID 440030ethyl (3R)-3-hydroxybutanoate수율 68.9%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
25 °C

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 KC1(0.5 gram) with rotary shaking at 25° C. Two grams of ethyl acetoacetate 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 approximately 48 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 1.4 grams of (R)-ethyl 3-hydroxybutyrate as a yellow oil.

후처리

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

출처 및 근거

ORD 기록
ord-4c4aed301a144958857f552ae9eeafec
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834261

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