Sodium Hydroxide → N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-phenylglycine

HRID 1940614

Reaktionsgleichung

Reaktionsgleichung von HRID 1940614
C[O:2][C:3](=[O:28])[CH2:4][N:5]([C:12](=[O:27])[CH2:13][CH2:14][C:15]1[S:16][C:17]2[C:23]([F:24])=[CH:22][C:21]([F:25])=[C:20]([F:26])[C:18]=2[N:19]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Na+]>O.O1CCOCC1>[F:26][C:20]1[C:18]2[N:19]=[C:15]([CH2:14][CH2:13][C:12]([N:5]([C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:4][C:3]([OH:28])=[O:2])=[O:27])[S:16][C:17]=2[C:23]([F:24])=[CH:22][C:21]=1[F:25]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 21463503N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-phenylglycine methyl ester

Produkt 1

HCID 21463543N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-phenylglycineAusbeute 53,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-phenylglycine methyl ester (420 mg, 1 mmol) in a mixture of water (3 ml) and dioxane (6 ml) was added dropwise 2N sodium hydroxide (1.2 ml) with stirring under ice cooling and the mixture was stirred for 1 hour at room temperature. The reaction mixture was then diluted with water and washed with ether. The aqueous layer was acidified with 7% hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, then dried and evaporated to yield a residue, which was recrystallized from ethyl acetate-isopropyl ether to give N-[3-(4,5,7-trifluorobenzothiazol-2-yl)propionyl]-N-phenylglycine 210 mg, 52%) as a colorless powder.

Aufarbeitung

  1. stirringthe mixture was stirred for 1 hour at room temperature
  2. washwashed with ether
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. customto yield a residue, which
  8. customwas recrystallized from ethyl acetate-isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6451ce8531cc4ddbaba07868224bc95b
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05700819

Verknüpfte Notizen

Wird geladen…