4-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid tert-butyl ester → 4-([3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid

HRID 581161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 581161
C([O:5][C:6](=[O:34])[CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[N:16]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]([CH2:27][CH3:28])=[C:14]2[C:29](=[O:33])[C:30]([NH2:32])=[O:31])(C)(C)C>C(Cl)Cl.FC(F)(F)C(O)=O>[NH2:32][C:30](=[O:31])[C:29]([C:14]1[C:13]2[C:17](=[CH:18][CH:19]=[C:11]([O:10][CH2:9][CH2:8][CH2:7][C:6]([OH:34])=[O:5])[CH:12]=2)[N:16]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:15]=1[CH2:27][CH3:28])=[O:33]

Komponenten

4

Edukt 1

HCID 108139834-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid tert-butyl ester

Produkt 1

HCID 99312854-([3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acidAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

A solution of 450 mg (0.97 mmol) of 4-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid tert-butyl ester in 75 mL of methylene chloride and 1 mL of trifluoroacetic acid was stirred at room temperature for 2.25 hours and concentrated at reduced pressure. The residue was chromatographed on silica gel and eluted with EtOAc to give 250 mg (63% yield) of 4-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-5-yl]oxy]butanoic acid, mp 173-175° C.

Aufarbeitung

  1. concentrationconcentrated at reduced pressure
  2. customThe residue was chromatographed on silica gel
  3. washeluted with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-446c98f1d30b49fb8252fe630a1b35ea
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919810

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