Reaktion #3437

Reaktionsgleichung

Oxalyl chloride

2-[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester

ammonia

→

2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid, methyl ester

Ausbeute 90.0%

Lösungsmittel

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water
2. 2
   Trocknendried (MgSO4)
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe residue was chromatographed on silica gel (eluted with EtOAc)

Vorschrift

Oxalyl chloride (0.16 mL, 1.9 mmol) was reacted with 480 mg (1.5 mmol) of dl-2-[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester and then reacted with anhydrous ammonia as in Example 1, Part F and the reaction product was dissolved in EtOAc, washed with water, dried (MgSO4) and concentrated. The residue was chromatographed on silica gel (eluted with EtOAc) to give 531 mg (90% yield) of dl-2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid, methyl ester, melting at approximately 175° C.

Quelle