Reaktion #65993

Reaktionsgleichung

compound

1-[(4-Chlorophenyl)methyl]-2-methyl-5-(2-benzothiazolylmethoxy)-1H-indole-3-acetic acid

ethyl chloroformate

ammonium hydroxide

→

title compound

Ausbeute 90.0%

5-(2-Benzothiazolylmethoxy)-1-[(4-chlorophenyl)methyl]-2-methyl-1H-indole-3-acetamide

Ausbeute 90.0%

Lösungsmittel

water

tetrahydrofuran

triethylamine

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONis added slowly
2. 2
   Extraktionis extracted with ethyl acetate (3×100 mL)
3. 3
   ExtraktionThe combined extract
4. 4
   Waschenis washed with 2N HCl (200 mL) and brine (200 mL)
5. 5
   Trocknendried over MgSO4
6. 6
   Einengenconcentrated
7. 7
   Sonstigeto give crude product (0.55 g)
8. 8
   SonstigeCrystallization from acetonitrile

Vorschrift

To a mixture containing the compound of Example 37(0.5 g, 1.05 mmol) in tetrahydrofuran (30 mL) and triethylamine (0.6 mL) at -10° C., is added slowly with stirring a solution of ethyl chloroformate (0.14 g, 1.29 mmol) in tetrahydrofuran (10 mL). After 30 minutes, 30% ammonium hydroxide (0.6 mL) is added and the mixture is stirred for 18 hours at 23° C. The mixture is diluted with water (100 mL) and is extracted with ethyl acetate (3×100 mL). The combined extract is washed with 2N HCl (200 mL) and brine (200 mL), dried over MgSO4 and concentrated to give crude product (0.55 g). Crystallization from acetonitrile gives pure title compound in 90% yield as a white solid, m.p. 169°-170° C.

Quelle