Reaktion #3476

Reaktionsgleichung

[[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-1H-indol-4-yl]0xy]acetic acid methyl ester

→

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

Ausbeute 62.3%

Lösungsmittel

NaOH

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated at reduced pressure
2. 2
   SonstigeThe aqueous layer was separated
3. 3
   Extraktionextracted with EtOAc
4. 4
   TrocknenThe EtOAc solution was dried (MgSO4)
5. 5
   Sonstigeevaporated
6. 6
   workup.STIRRINGthe residue stirred with EtOAc/ether
7. 7
   FiltrationThe insoluble material was filtered

Vorschrift

A mixture of 175 mg (0.36 mmol) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-1H-indol-4-yl]0xy]acetic acid methyl ester in 4 mL of 1N NaOH and 10 mL of MeOH was stirred for 0.5 hours, concentrated at reduced pressure and the residue taken up in EtOAc/water. The aqueous layer was separated, made acidic with 1N HCl to pH 2-3 and extracted with EtOAc. The EtOAc solution was dried (MgSO4), evaporated and the residue stirred with EtOAc/ether. The insoluble material was filtered to give 105 mg (62% yield) of [[3-(2-amino-1,2-dioxoethyl)-1-([1,1'-biphenyl]-2-ylmethyl)-2-cyclopropyl-1H-indol-4-yl]oxy]acetic acid, mp, 172°-174° C.

Quelle