Boron trifluoride → Anhydrodihydroartemisnin

HRID 480213

반응식

HRID 480213 반응식
[CH3:1][C@H:2]1[C@@H:11]2[CH2:12][CH2:13][C:14]3([CH3:18])[O:16][O:17][C@:10]42[C@H:5]([C@@H:6]([CH3:20])[C@@H:7](O)[O:8][C@@H:9]4[O:15]3)[CH2:4][CH2:3]1.B(F)(F)F>C(OCC)C>[CH3:1][C@H:2]1[C@@H:11]2[CH2:12][CH2:13][C@@:14]3([CH3:18])[O:16][O:17][C@:10]42[C@H:5]([C:6]([CH3:20])=[CH:7][O:8][C@@H:9]4[O:15]3)[CH2:4][CH2:3]1

참가 물질

4

반응물 2

HCID 6356Boron trifluorideHCID 456410Npc182939

생성물 1

HCID 393517Anhydrodihydroartemisnin수율 172.5%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of dihydroartemisinin (10.4 g) in diethyl ether (550 ml) at room temperature under nitrogen was added dropwise boron trifluoride dietherate (1.0 ml). The solution was stirred at room temperature overnight, washed with 5% NaHCO3 solution (3×100 ml); dried (MgSO4) and concentrated in vacuo. The residue was then purified by flash chromatography (SiO2; 10% ethyl acetate/hexanes) to give 9,10-anhydrodehydroartemisinin as a white solid (16.8 g, 97%). δH: 6.20 (1H, q, J=1.41 Hz, H-10), 5.55 (1H, s, H-12), 2.33-3.50 (1H, m), 1.03-2.18 (10H, m), 1.60 (3H, d, J=1.41 Hz, H16), 1.44 (3H, s, H-14), 1.00 (3H, d, J=5.98 Hz, H-15).

후처리

  1. washwashed with 5% NaHCO3 solution (3×100 ml)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was then purified by flash chromatography (SiO2; 10% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-ab8b8f820ff84f709c1de311e8cf528a
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649647B1

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