Hydrochloric Acid → N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-2-methyl-propionamide

HRID 2068737

Reaktionsgleichung

Reaktionsgleichung von HRID 2068737
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12]([C:14]([O:17]C(=O)C)([CH3:16])[CH3:15])=[O:13])[NH:7][C:6](=[O:21])[CH2:5]2.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH:11][C:12](=[O:13])[C:14]([OH:17])([CH3:16])[CH3:15])[NH:7][C:6](=[O:21])[CH2:5]2

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59250100acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-1-methyl-ethyl ester

Produkt 1

HCID 59250047N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-2-methyl-propionamideAusbeute 59,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Acetic acid 1-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-ylcarbamoyl)-1-methyl-ethyl ester 11a (2.035 mg, 6.9 mmol) was dissolved in 20 mL of methanol under stirring at room temperature, and 20 mL of sodium hydroxide solution (0.7 M) was then added to the solution. The reaction solution was stirred for 4 hours. The reaction was completed until TLC showed the disappearance of starting materials, and the above solution was neutralized with hydrochloric acid (1 M) and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and dried to give N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-hydroxy-2-methyl-propionamide 11b (900 mg, yield 59.2%) as a white solid.

Aufarbeitung

  1. stirringThe reaction solution was stirred for 4 hours
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c4dc06b3c2b84397bc6c68ecbdcea45f
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299069B2

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