Ethanol → Ethyl (S)-[[1-(2-[[(1-amino-6-isoquinolinyl)carbonyl]amino]-1-oxopropyl)piperidin-4-yl]oxy]acetic acid hydrochloride

HRID 1279027노트

반응식

HRID 1279027 반응식
[ClH:1].[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([NH:15][C@@H:16]([CH3:30])[C:17]([N:19]3[CH2:24][CH2:23][CH:22]([O:25][CH2:26][C:27]([OH:29])=[O:28])[CH2:21][CH2:20]3)=[O:18])=[O:14])=[CH:10][CH:11]=2)[CH:6]=[CH:5][N:4]=1.S(=O)(=O)(O)O.[OH-].[Na+].C(=O)([O-])O.[Na+].[CH2:43](O)[CH3:44]>[Cl-].[Na+].O.ClCCl>[ClH:1].[CH2:43]([C@H:26]([O:25][CH:22]1[CH2:21][CH2:20][N:19]([C:17](=[O:18])[CH:16]([NH:15][C:13]([C:9]2[CH:8]=[C:7]3[C:12](=[CH:11][CH:10]=2)[C:3]([NH2:2])=[N:4][CH:5]=[CH:6]3)=[O:14])[CH3:30])[CH2:24][CH2:23]1)[C:27]([OH:29])=[O:28])[CH3:44]

참가 물질

8

반응물 5

HCID 702EthanolHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 69780722(S)-[[1-(2-[[(1-amino-6-isoquinolinyl)carbonyl]amino]-1-oxopropyl)piperidin-4-yl]oxy]acetic acid hydrochloride

생성물 1

HCID 86758500Ethyl (S)-[[1-(2-[[(1-amino-6-isoquinolinyl)carbonyl]amino]-1-oxopropyl)piperidin-4-yl]oxy]acetic acid hydrochloride

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 57417360Sodium chloride; water용매

실험 절차

To a stirred solution of 394 mg of (S)-[[1-(2-[[(1-amino-6-isoquinolinyl)carbonyl]amino]-1-oxopropyl)piperidin-4-yl]oxy]acetic acid hydrochloride in 10 mL of ethanol at 0° C. was added 0.55 mL of sulfuric acid (95-98%). The reaction mixture was allowed to warm to room temperature and after 2 hours 5 mL of 2N aqueous sodium hydroxide, 20 mL of brine, 20 mL of 5% aqueous sodium hydrogencarbonate and 40 mL of dichloromethane was added. The organic layer was separated and the aqueous layer was extracted three times with dichloromethane. The combined organic layers were dried (sodium sulfate) and concentrated. Purification using column chromatography (silica gel, dichloromethane:ethanol =9:1) and lyophilisation (t-butanol/hydrochloric acid) yielded 265 mg of the title compound.

후처리

  1. additionwas added
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted three times with dichloromethane
  4. dry with materialThe combined organic layers were dried (sodium sulfate)
  5. concentrationconcentrated
  6. customPurification

출처 및 근거

ORD 기록
ord-2f2e6c15f92d46958dbdbc88bea329bd
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06444672B1

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