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

HRID 1279027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1279027
[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]

Komponenten

8

Edukt 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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2f2e6c15f92d46958dbdbc88bea329bd
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06444672B1

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