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 2225468Notes

Reaction equation

HRID 2225468 reaction equation
[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]

Participants

6

Reactant 2

HCID 5825Dextroamphetamine sulfateHCID 44259Staurosporine

Product 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-diolYield 59%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 14798Sodium HydroxideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-10fbcaf5b50f467480683f5fb9cc6a2d
Source dataset
uspto-grants-1994_09
Patent number
US05344926

Reaction notes

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