Citric Acid → 1-Benzyloxycarbonyl-4-[N-(5-isoquinolinesulfonyl)tyrosyl]homopiperazine

HRID 5731

反応式

HRID 5731 の反応式
[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

参加物

7

反応物 4

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 538376321-Benzyloxycarbonyl-4-[N,O-Bis(5-Isoquinolinesulfonyl)Tyrosyl]Homopiperazine

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fa570eec38af45bdaa6d75337b1e1aef
出典データセット
uspto-grants-1993_09
特許番号
US05245034

関連ノート

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