Reaktion #362325

Reaktionsgleichung

hydrochloric acid

methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate

cyclopentylacetic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

title compound

Ausbeute 73.0%

Methyl 4-[5-(2-cyclopentylacetamido)-1-methylindol-3-ylmethyl]-3-methoxybenzoate

Ausbeute 73.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe separated aqueous layer extracted with dichloromethane (3×25 ml.)
2. 2
   Waschenthe combined organic extracts washed with water, brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residual oil was crystallized from ethyl acetate

Vorschrift

A mixture of methyl 4-(5-amino-1-methylindol-3-ylmethyl)-3-methoxybenzoate (D) (0.57 g.), cyclopentylacetic acid (0.23 g.), 4-(dimethylamino)pyridine (0.22 g.), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.343 g.), was dissolved in dichloromethane (25 ml.), under an atmosphere of nitrogen, and stirred at room temperature for 18 hours. The mixture was poured into 1M hydrochloric acid (25 ml.), the separated aqueous layer extracted with dichloromethane (3×25 ml.), the combined organic extracts washed with water, brine, dried (MgSO4) and evaporated. The residual oil was crystallized from ethyl acetate to give the title compound (0.555 g. 73%) as a white powder; m.p. 180°-181° C.; partial NMR (250 MHz, DMSO-d6 ): 1.17(m,2H); 1.4-1.8 (m,6H); 2.25(m,3H); 3.70(s,3H, NMe); 3.82(s,3H, OMe); 3.92(s,3H, OMe); 3.97(s,2H, ArCH2); 9.62(br s, 1H, NH).

Quelle