Hydrochloric Acid → HCID 89933016, Verbindung

HRID 1775447Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1775447
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][C:5]=1[C:16]([OH:18])=[O:17].C(N(C(C)C)CC)(C)C.[C:28](OC(=O)C)(=[O:30])[CH3:29].[OH-].[Na+].Cl>O1CCCC1>[C:28]([NH:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([O:13][CH3:14])[CH:11]=2)[NH:6][C:5]=1[C:16]([OH:18])=[O:17])(=[O:30])[CH3:29]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 6164323-(2-Aminoethyl)-6-fluoro-5-methoxy-1H-indole-2-carboxylic acid

Produkt 1

HCID 89933016HCID 89933016, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 3-(2-aminoethyl)-6-fluoro-5-methoxy-1H-indole-2-carboxylic acid (1.90 g) and tetrahydrofuran (38.0 mL) were added diisopropylethylamine (6.45 mL) and acetic anhydride (1.42 mL), followed by stirring at room temperature overnight. To the reaction mixture was added a 1 M aqueous sodium hydroxide solution (50.0 mL), followed by stirring for 1 hour and acidifying by the addition of 1 M hydrochloric acid (90.0 mL). This mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine and then dried over anhydrous sodium sulfate. The insoluble materials were separated by filtration and the filtrate was concentrated under reduced pressure to obtain 3-(2-acetamidoethyl)-6-fluoro-5-methoxy-1H-indole-2-carboxylic acid (2.21 g) as a pale yellow solid.

Aufarbeitung

  1. stirringby stirring for 1 hour
  2. extractionThis mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble materials were separated by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c16d0860e4e44193b2ac7b81bc7fc2ca
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09260445B2

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