L-Serine → 2-acetamido-3-(6-chloro-5-fluoro-1H-indol-3-yl)propanoic acid

HRID 555339Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 555339
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][C:3]=1[F:11].[CH3:12][C:13](OC(C)=O)=[O:14].[NH2:19][C@H:20]([C:23]([OH:25])=[O:24])[CH2:21]O>CC(O)=O>[C:13]([NH:19][CH:20]([CH2:21][C:6]1[C:5]2[C:9](=[CH:10][C:2]([Cl:1])=[C:3]([F:11])[CH:4]=2)[NH:8][CH:7]=1)[C:23]([OH:25])=[O:24])(=[O:14])[CH3:12]

Komponenten

5

Edukt 3

HCID 5951L-SerineHCID 7918Acetic AnhydrideHCID 27736486-Chloro-5-fluoro-1H-indole

Produkt 1

HCID 579487332-acetamido-3-(6-chloro-5-fluoro-1H-indol-3-yl)propanoic acidAusbeute 37 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 6-chloro-5-fluoroindole (1.8 g, 10.8 mmol) and Ac2O (10 mL) in AcOH (30 mL) was added L-serine (2.2 g, 20.9 mmol), the mixture was heated to 80° C. After TLC indicated the reaction was complete, the mixture was cooled to 0° C., neutralized to pH 11, and washed with MTBE. The aqueous phase was acidified to pH 2 and extracted with EtOAc. The combined organic layers were washed with water and brine, dried with Na2SO4, filtered, and concentrated. The residue was purified with chromatography (Petroleum ether/EtOAc 1:1) to give 2-acetylamino-3-(6-chloro-5-fluoro-1H-indol-3-yl)-proprionic acid as a light yellow solid (1.2 g, 37% yield).

Aufarbeitung

  1. temperaturethe mixture was cooled to 0° C.
  2. washwashed with MTBE
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified with chromatography (Petroleum ether/EtOAc 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-dd62cebfdb2a4dbe8bf5ac666e609094
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08053442B2

Notizen zur Reaktion

Wird geladen…