ubiquitin cross-reactive protein → 1-Benzyloxycarbonyl-4-[N-(5-isoquinolinesulfonyl)tyrosyl]homopiperazine

HRID 5731

反应方程式

HRID 5731 反应方程式
[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:55])[C@H:19]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([O:41]S(C3C4C=CN=CC=4C=CC=3)(=O)=O)=[CH:37][CH:36]=2)[NH:20][S:21]([C:24]2[C:25]3[CH:26]=[CH:27][N:28]=[CH:29][C:30]=3[CH:31]=[CH:32][CH:33]=2)(=[O:23])=[O:22])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(=O)(O)[O-].[Na+]>CO.O1CCCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:55])[C@H:19]([CH2:34][C:35]2[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=2)[NH:20][S:21]([C:24]2[C:25]3[CH:26]=[CH:27][N:28]=[CH:29][C:30]=3[CH:31]=[CH:32][CH:33]=2)(=[O:22])=[O:23])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参与物

7

反应物 4

HCID 311ubiquitin cross-reactive proteinHCID 14798二甲基对苯二胺二盐酸HCID 516892碳酸氢钠HCID 538376321-Benzyloxycarbonyl-4-[N,O-Bis(5-Isoquinolinesulfonyl)Tyrosyl]Homopiperazine

产物 1

HCID 228421921-Benzyloxycarbonyl-4-[N-(5-isoquinolinesulfonyl)tyrosyl]homopiperazine收率 74.7%

试剂、催化剂与溶剂 2

HCID 887(5BETA,17BETA)-17-羟基-17-(甲基-D3)-2'H-雄甾-2-烯并[3,2-C]吡唑-5'(1'H)-酮溶剂2 次HCID 8028四氢呋喃溶剂

实验过程

5.50 g of the amorphous compound obtained in Example 122 was dissolved in 30 ml of methanol and 30 ml of tetrahydrofuran, to the solution was added 60 ml of 1N sodium hydroxide, and the mixture was refluxed for 2 hours and then cooled. The reaction mixture was acidified with citric acid and then alkalized with sodium bicarbonate, resulting insoluble matter was dissolved with a small amount of methanol, and the solution was extracted twice with 400 ml of chloroform. The extract was dried over magnesium sulfate and evaporated to remove the solvent under a reduced pressure, and resulting residue was applied to a silica gel column and eluted with chloroform/methanol (20:1) to obtain 3.1 g of the title compound in a colorless amorphous form.

后处理

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperaturecooled
  3. customresulting insoluble matter
  4. extractionthe solution was extracted twice with 400 ml of chloroform
  5. dry with materialThe extract was dried over magnesium sulfate
  6. customevaporated
  7. customto remove the solvent under a reduced pressure
  8. customresulting residue
  9. washeluted with chloroform/methanol (20:1)

来源与证据

ORD记录
ord-fa570eec38af45bdaa6d75337b1e1aef
来源数据集
uspto-grants-1993_09
专利号
US05245034

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