Hydrochloric Acid → HCID 71737074, Verbindung

HRID 1481058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1481058
CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].Cl.[NH2:26][C@@H:27]([CH:32]([CH3:34])[CH3:33])[CH2:28][C:29]([OH:31])=[O:30].C[O-].[Na+].Cl>COCCO>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:26][CH:27]([CH:32]([CH3:34])[CH3:33])[CH2:28][C:29]([OH:31])=[O:30])=[O:4])[N:6]=1)#[N:24]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 2761557L-beta-Homovaline hydrochlorideHCID 10942334Sodium MethoxideHCID 89812860Methyl 1-cyano-4-hydroxy-7-phenoxyisoquinoline-3-carboxylate

Produkt 1

HCID 71737074HCID 71737074, VerbindungAusbeute 13,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of 1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (50 mg, 0.16 mmole), (R)-3-amino-4-methylpentanoic acid hydrochloride (52 mg, 0.31 mmole) (Chem-Impex International Inc., Wood Dale Ill.), and sodium methoxide (25 mg, 0.46 mmole) in 2-methoxyethanol was stirred at 130° C. for two hours before it was cooled to room temperature and acidified with 1 N HCl. The mixture was partitioned between dichloromethane and water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of 1% acetic acid, ethyl acetate and hexanes to give the title compound as a yellow solid (9 mg): MS: (+) m/z 420.06 (M+1), (−) m/z 418.02 (M−1).

Aufarbeitung

  1. temperaturewas cooled to room temperature
  2. customThe mixture was partitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel with a gradient of 1% acetic acid, ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9c33426826a14dd19cea39ca411c04e7
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409892B2

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