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 2225468노트

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HRID 2225468 반응식
[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]

참가 물질

6

반응물 2

HCID 5825Dextroamphetamine SulfateHCID 44259Staurosporine

생성물 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-diol수율 59%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 8857Ethyl Acetate용매HCID 14798Sodium Hydroxide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-10fbcaf5b50f467480683f5fb9cc6a2d
출처 데이터셋
uspto-grants-1994_09
특허 번호
US05344926

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