Dextroamphetamine Sulfate → 8-Methoxy-9-methyl-7-(methylamino)-6,7,8,9-tetrahydro-5H,14H-5,9-epoxy-4b,9a,15-triazadibenzo[b,h]cyclonona[1,2,3,4-jkl]cyclopenta[e]-as-indacene-14,16-diol

HRID 2225468Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2225468
[CH3:1][C@:2]12[N:18]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:25]4[C:26]5[CH2:31][NH:30][C:28](=[O:29])[C:27]=5[C:15]5=[C:16]([C:17]=43)[N:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=35)[C@H:6]([O:7]1)[CH2:5][C@@H:4]([NH:32][CH3:33])[C@H:3]2[O:34][CH3:35].C[C@H](N)CC1C=CC=CC=1.C[C@H](N)CC1C=CC=CC=1.[OH:56]S(O)(=O)=O>CS(C)=O.[OH-].[Na+].C(OCC)(=O)C>[CH3:1][C@:2]12[N:18]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:25]4[C:26]5[C@H:31]([OH:56])[NH:30][C:28](=[O:29])[C:27]=5[C:15]5=[C:16]([C:17]=43)[N:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=35)[C@H:6]([O:7]1)[CH2:5][C@@H:4]([NH:32][CH3:33])[C@H:3]2[O:34][CH3:35]

Komponenten

6

Edukt 2

HCID 5825Dextroamphetamine SulfateHCID 44259Staurosporine

Produkt 1

HCID 30785198-Methoxy-9-methyl-7-(methylamino)-6,7,8,9-tetrahydro-5H,14H-5,9-epoxy-4b,9a,15-triazadibenzo[b,h]cyclonona[1,2,3,4-jkl]cyclopenta[e]-as-indacene-14,16-diolAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 679Dimethyl SulfoxideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

100 mg (0.21 mmol) of staurosporine (commercially available from Kyowa Medex Co., Ltd., Japan) was dissolved in a mixture of 4 ml of DMSO and 1 ml of 2N sodium hydroxide. The solution was stirred overnight at room temperature. The reaction solution was diluted with ethyl acetate, washed with water and brine in order, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography using the elution with 0%, 4%, 6%, and 10% acetone-containing chloroform in order to obtain 60 mg (yield: 59%) of UCN-01.

Aufarbeitung

  1. washwashed with water and brine in order
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. customthe residue was purified by silica gel column chromatography
  5. washthe elution with 0%, 4%, 6%, and 10% acetone-
  6. additioncontaining chloroform in order

Quellen und Nachweise

ORD-Eintrag
ord-10fbcaf5b50f467480683f5fb9cc6a2d
Quelldatensatz
uspto-grants-1994_09
Patentnummer
US05344926

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