Reaktion #3465

Reaktionsgleichung

[[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-1H-indol-4-yl]oxy]acetic acid methyl ester

→

[[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-1H-indol-4-yl]oxy]acetic acid

Ausbeute 59.3%

Lösungsmittel

NaOH

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturto maintain
3. 3
   Temperaturreflux for 0.67 hours
4. 4
   Einengenconcentrated at reduced pressure
5. 5
   SonstigeThe aqueous layer was separated
6. 6
   Extraktionextracted with EtOAc
7. 7
   TrocknenThe EtOAc solution was dried (MgSO4)
8. 8
   Sonstigeevaporated
9. 9
   Sonstigethe residue crystallized from MeOH

Vorschrift

A mixture of 600 mg (1.3 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-1H-indol-4-yl]oxy]acetic acid methyl ester in 8 mL of 1N NaOH and 20 mL of MeOH was heated to maintain reflux for 0.67 hours, concentrated at reduced pressure and the residue taken up in EtOAc/water. The aqueous layer was separated, made acidic with 1N HCl and extracted with EtOAc. The EtOAc solution was dried (MgSO4) and evaporated and the residue crystallized from MeOH to give 352 mg (59% yield) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-ethyl-1H-indol-4-yl]oxy]acetic acid, mp, 211°-214° C.

Quelle