2-Ethoxy-2-hydroxyacetic acid p-nitrobenzyl ester → 2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester

HRID 1710246

Reaktionsgleichung

Reaktionsgleichung von HRID 1710246
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][O:9][C:10](=[O:16])[CH:11]([O:13]CC)O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:19]([S:22][C@H:23]1[NH:26][C:25](=[O:27])[C@@H:24]1[O:28][CH3:29])(=[O:21])[CH3:20]>C1(C)C=CC=CC=1.CN(C)C=O>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10](=[O:16])[CH:11]([N:26]2[C@H:23]([S:22][C:19](=[O:21])[CH3:20])[C@@H:24]([O:28][CH3:29])[C:25]2=[O:27])[OH:13])=[CH:17][CH:18]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 2

HCID 110433162-Ethoxy-2-hydroxyacetic acid p-nitrobenzyl esterHCID 56630779(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidine

Produkt 1

HCID 566076512-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.15 g of 2-ethoxy-2-hydroxyacetic acid p-nitrobenzyl ester and 4 g of molecular sieves A4are added to a solution of 350 mg of (3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidine in a mixture of 24 ml of absolute toluene and 6 ml of absolute dimethylformamide and the mixture is stirred overnight at room temperature under nitrogen. The molecular sieves are filtered off and the filtrate is concentrated by evaporation in vacuo. The residue is chromatographed over silica gel, and the title compound is obtained by eluting with toluene and toluene/ethyl acetate (19:1).

Aufarbeitung

  1. filtrationThe molecular sieves are filtered off
  2. concentrationthe filtrate is concentrated by evaporation in vacuo
  3. customThe residue is chromatographed over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-238988504a214b94aa1f9eb38d617296
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04952690

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