Potassium Carbonate → 8-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinone

HRID 1634727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1634727
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:20])=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH2:15][CH2:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+](C1C=C(S(O[CH2:34][C@H:35]2[O:37][CH2:36]2)(=O)=O)C=CC=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:20][CH2:34][C@@H:35]2[CH2:36][O:37]2)=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH2:15][CH2:14]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 146490Benzenesulfonic acid, 3-nitro-, (2S)-2-oxiranylmethyl esterHCID 127517378-(Benzyloxy)-5-hydroxy-3,4-dihydroquinolin-2(1H)-one

Produkt 1

HCID 233813448-(Benzyloxy)-5-[(2S)oxiranylmethoxy]-3,4-dihydro-2(1H)-quinolinoneAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6569Methyl Ethyl KetoneLösungsmittel

Versuchsvorschrift

A mixture of 8-(benzyloxy)-5-hydroxy-3,4-dihydro-2(1H)-quinolinone (0.20 g, 0.743 mmol), (S)-(+)-glycidyl 3-nitrobenzenesulfonate (0.193 g, 0.743 mmol) and potassium carbonate (0.113 g, 0.817 mmol) in 2-butanone (10 mL) was heated at reflux for 16 hours. The solvent was removed in vacuo and the residue purified by flash chromatography (chloroform-methanol, 50:1) to yield the title compound (0.210 g, 0.61 mmol).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue purified by flash chromatography (chloroform-methanol, 50:1)

Quellen und Nachweise

ORD-Eintrag
ord-60d95559de3842d6aeac341fa2e20646
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06506901B2

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