4-Acetylthio-2-azetidinone → p-Nitrobenzyl 2-(4-acetylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate

HRID 1680321Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1680321
O.[C:2]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(=[O:5])[CH:3]=[O:4].[C:17]([S:20][CH:21]1[NH:24][C:23](=[O:25])[CH2:22]1)(=[O:19])[CH3:18]>C1C=CC=CC=1>[C:17]([S:20][CH:21]1[N:24]([CH:3]([OH:4])[C:2]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[O:5])[C:23](=[O:25])[CH2:22]1)(=[O:19])[CH3:18]

Komponenten

4

Edukt 2

HCID 131320584-Acetylthio-2-azetidinoneHCID 21934455p-Nitrobenzyl glyoxylate hydrate

Produkt 1

HCID 13132061p-Nitrobenzyl 2-(4-acetylthio-2-oxo-1-azetidinyl)-2-hydroxyacetateAusbeute 115,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

p-Nitrobenzyl glyoxylate hydrate (63.4 g., 0.278 mole) was added to a solution of 4-acetylthio-2-azetidinone (36.2 g., 0.250 mole) in 1200 ml. of benzene. The mixture was refluxed for 17 hours in a Dean Stark apparatus. The solution was concentrated on a rotary evaporator to give the title product as a yellow oil (102 g., 100%). This oil was found to be identical with the product of Preparation 2A-1.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 17 hours in a Dean Stark apparatus
  2. concentrationThe solution was concentrated on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-8b7493330a5f44478ff9bb6ace064305
Quelldatensatz
uspto-grants-1981_06
Patentnummer
US04272437

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