Acetic Acid → Npc182939

HRID 1085933

Reaktionsgleichung

Reaktionsgleichung von HRID 1085933
[CH3:1][C@H:2]1[C@@H:12]2[CH2:13][CH2:14][C@@:15]3([CH3:19])[O:17][O:18][C@:11]42[C@H:5]([C@@H:6]([CH3:20])[C:7]([O:9][C@@H:10]4[O:16]3)=[O:8])[CH2:4][CH2:3]1.[BH4-].[Na+].CC(O)=O>CO.O>[CH3:1][C@H:2]1[C@@H:12]2[CH2:13][CH2:14][C:15]3([CH3:19])[O:17][O:18][C@:11]42[C@H:5]([C@@H:6]([CH3:20])[C@@H:7]([OH:8])[O:9][C@@H:10]4[O:16]3)[CH2:4][CH2:3]1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 68827ArtemisininHCID 4311764Sodium borohydride

Produkt 1

HCID 456410Npc182939Ausbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of qinghaosu (I) (240 g, 0.85 mol) in 12 l MeOH was added NaBH4 (240 g, 6.34 mol) over a period of 2 h keeping the reaction mixture at 0°-5° C. After an additional stirring for 1.30 h under the same conditions, the mixture was neutralized with 375 ml AcOH maintaining the temperature in the range of 0°-5° C. and subsequently diluted with 24 l water. After stirring for 1 h at 0°-1° C., the white precipitate formed was collected and washed with 700 ml water-MeOH (2:1, 0°-5° C.) The filtrate was stirred for 14 h at 0° C. The small amount of material precipitated was collected and washed with H2O--MeOH (2:1, 2×30 ml). The wet crops were combined and dissolved in 7 l CH2Cl2. After drying on magnesium sulphate (120 g) and evaporation of the solvent, 212 g (88%) of (II) was obtained: mp 149°-153° C.

Aufarbeitung

  1. customat 0°-5° C
  2. customin the range of 0°-5° C.
  3. stirringAfter stirring for 1 h at 0°-1° C.
  4. customthe white precipitate formed
  5. customwas collected
  6. washwashed with 700 ml water-MeOH (2:1, 0°-5° C.) The filtrate
  7. stirringwas stirred for 14 h at 0° C
  8. customThe small amount of material precipitated
  9. customwas collected
  10. washwashed with H2O--MeOH (2:1, 2×30 ml)
  11. dissolutiondissolved in 7 l CH2Cl2
  12. customAfter drying on magnesium sulphate (120 g) and evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-6a664a66efdc48ae976c3e64effbdedd
Quelldatensatz
uspto-grants-1991_04
Patentnummer
US05011951

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