Water → p-Nitrobenzyl 2-hydroxy-2-(4-methylthio-2-azetidinon-1-yl)acetate

HRID 980959Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 980959
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].[CH3:17][S:18][CH:19]1[NH:22][C:21](=[O:23])[CH2:20]1.O>C1C=CC=CC=1>[OH:4][CH:3]([N:22]1[CH:19]([S:18][CH3:17])[CH2:20][C:21]1=[O:23])[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]

Komponenten

5

Edukt 3

HCID 962WaterHCID 126772484-(Methylsulfanyl)azetidin-2-oneHCID 21934455p-Nitrobenzyl glyoxylate hydrate

Produkt 1

HCID 20220832p-Nitrobenzyl 2-hydroxy-2-(4-methylthio-2-azetidinon-1-yl)acetateAusbeute 106,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

p-Nitrobenzyl glyoxylate monohydrate (1.11 g, 4.87 mmoles) was added to a solution of 4-methylthio-2-azetidinone (570 mg, 4.87 mmoles) in benzene (30 ml) and the resulting solution was heated, whilst the water produced was removed by azeotropic distillation. After the water had been distilled off completely, the mixture was concentrated and heated at a bath temperature of 100°-110° C. for 12 hours. The solvent was then distilled off under reduced pressure to give 1.69 g of the desired compound as a viscous oil. This product may be employed in subsequent reactions without purification, although it contains a small amount of the starting compound.

Aufarbeitung

  1. customproduced
  2. customwas removed by azeotropic distillation
  3. distillationAfter the water had been distilled off completely
  4. concentrationthe mixture was concentrated
  5. temperatureheated at a bath temperature of 100°-110° C. for 12 hours
  6. distillationThe solvent was then distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c4b35f144882476cb8d03696e23ab9fc
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04639441

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