Citric Acid → 1-(6-Chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxamide Hydrochloride

HRID 1700374ノート

反応式

HRID 1700374 の反応式
C(OC([O-])=O)(=O)OC(C)(C)C.Cl.[Cl:13][C:14]1[CH:15]=[C:16]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22]1[CH:21]([C:27]3([C:31](OCC)=[O:32])[CH2:30][CH2:29][CH2:28]3)[NH:20][CH2:19][CH2:18][C:17]2=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.ClC(OCC)=O.[OH-].[NH4+:56]>O1CCOCC1.O.[OH-].[Na+].O1CCCC1.CN1CCOCC1>[ClH:13].[Cl:13][C:14]1[CH:15]=[C:16]2[C:24](=[CH:25][CH:26]=1)[NH:23][C:22]1[CH:21]([C:27]3([C:31]([NH2:56])=[O:32])[CH2:28][CH2:29][CH2:30]3)[NH:20][CH2:19][CH2:18][C:17]2=1

参加物

11

反応物 5

HCID 311Citric AcidHCID 10928Ethyl chloroformateHCID 14923Ammonium HydroxideHCID 18317933Ethyl 1-(6-chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylate HydrochlorideHCID 22064466Tert-butyldicarbonate

生成物 1

HCID 183179441-(6-Chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxamide Hydrochloride

試薬・触媒・溶媒 5

HCID 962Water溶媒2 回HCID 79724-Methylmorpholine溶媒HCID 8028Tetrahydrofuran溶媒HCID 14798Sodium Hydroxide溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
-10 °C

実験手順

0.8 g of tert-butyl pyrocarbonate is added at 0° C. to a solution of 1 g of the compound of Example 1 in 20 ml of dioxane, 20 ml of water and 10 ml of 1M sodium hydroxide solution. After reaction for 4 hours, the reaction mixture is diluted by the addition of water and acidified with a 5% citric acid solution. After extraction with ethyl acetate, drying the organic phases, and concentration under reduced pressure, the residue obtained is diluted with 50 ml of tetrahydrofuran and 0.5 ml of N-methylmorpholine. After cooling the mixture to −10° C., 0.3 ml of ethyl chloroformate are added, followed by 0.2 ml of a 28% ammonium hydroxide solution. After reaction for 12 hours, the solvent is distilled off. The residue is then taken up in a water/dichloromethane mixture. After decanting, drying and concentrating under reduced pressure, the residue is treated with a solution of ethanol and ethereal hydrogen chloride, enabling the desired product to be obtained in the form of the hydrochloride.

後処理

  1. customAfter reaction for 4 hours
  2. extractionAfter extraction with ethyl acetate
  3. customdrying
  4. concentrationthe organic phases, and concentration under reduced pressure
  5. customthe residue obtained
  6. customAfter reaction for 12 hours
  7. distillationthe solvent is distilled off
  8. customAfter decanting
  9. customdrying
  10. concentrationconcentrating under reduced pressure
  11. additionthe residue is treated with a solution of ethanol and ethereal hydrogen chloride

出典と根拠

ORDレコード
ord-5262ac8c823f415c88bf6de4434cf90e
出典データセット
uspto-grants-2002_02
特許番号
US06350757B1

反応ノート

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