Hydrogen Bromide → 9-Bromo camptothecin

HRID 2229190

Reaktionsgleichung

Reaktionsgleichung von HRID 2229190
N([O-])=O.[Na+].[CH3:5][CH2:6][C@@:7]1([OH:31])[C:12](=[O:13])[O:11][CH2:10][C:9]2[C:14]([N:16]3[C:28](=[CH:29][C:8]1=2)[C:27]1[N:26]=[C:25]2[C:20]([C:21](N)=[CH:22][CH:23]=[CH:24]2)=[CH:19][C:18]=1[CH2:17]3)=[O:15].[BrH:32]>O>[CH3:5][CH2:6][C@@:7]1([OH:31])[C:12](=[O:13])[O:11][CH2:10][C:9]2[C:14]([N:16]3[C:28](=[CH:29][C:8]1=2)[C:27]1[N:26]=[C:25]2[C:20](=[CH:19][C:18]=1[CH2:17]3)[C:21]([Br:32])=[CH:22][CH:23]=[CH:24]2)=[O:15]

Komponenten

5

Edukt 3

HCID 260Hydrogen Bromide2×HCID 724029-AminocamptothecinHCID 23668193Sodium Nitrite

Produkt 1

HCID 102960989-Bromo camptothecinAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

215 g of NaNO2 in 40 mL of H2O were dropped at 5° C. into a solution of 9 g of 9-amino-camptothecin in 850 mL of 16% HBr. After 1 hr at room temperature the solution was dropped in a flask containing 19 g of CuBr in 200 mL of 16% HBr at 70° C. The reaction mixture was kept at 70° C. for 2 hrs, then it was poured into cold water. The precipitate was filtered and the mother liquors were extracted with CH2Cl2; the organic extract, dried and evaporated, was combined with the precipitate and purified by flash chromatography (eluent: CH2Cl2/CH3OH=95/5) to give 8.19 g of the title product (HPLC assay: 97.3%).

Aufarbeitung

  1. additionAfter 1 hr at room temperature the solution was dropped in a flask
  2. filtrationThe precipitate was filtered
  3. extractionthe mother liquors were extracted with CH2Cl2
  4. customthe organic extract, dried
  5. customevaporated
  6. custompurified by flash chromatography (eluent: CH2Cl2/CH3OH=95/5)

Quellen und Nachweise

ORD-Eintrag
ord-80729407426642d0883e4aacd5e4939b
Quelldatensatz
uspto-grants-2002_07
Patentnummer
US06420379B1

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