Benzene → p-Nitrobenzyl 2(4-ethylthio-3-p-nitrobenzyloxycarbonyloxyethyl-2-oxo-1-azetidinyl)-2-hyroxyacetate

HRID 2291004

Reaktionsgleichung

Reaktionsgleichung von HRID 2291004
[CH2:1]([S:3][CH:4]1[NH:7][C:6](=[O:8])[CH:5]1[CH2:9][CH2:10][O:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[O:13])[CH3:2].C([O:27][CH:28](O)[C:29]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=1)=[O:30])C.C1C=CC=CC=1>O>[CH2:1]([S:3][CH:4]1[N:7]([CH:28]([OH:27])[C:29]([O:31][CH2:32][C:33]2[CH:34]=[CH:35][C:36]([N+:39]([O-:41])=[O:40])=[CH:37][CH:38]=2)=[O:30])[C:6](=[O:8])[CH:5]1[CH2:9][CH2:10][O:11][C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=1)=[O:13])[CH3:2]

Komponenten

5

Edukt 3

HCID 241BenzeneHCID 110433162-Ethoxy-2-hydroxyacetic acid p-nitrobenzyl esterHCID 537511124-Ethylthio-3-p-nitrobenzyloxycarbonyloxyethyl-2-oxo-azetidine

Produkt 1

HCID 54314145p-Nitrobenzyl 2(4-ethylthio-3-p-nitrobenzyloxycarbonyloxyethyl-2-oxo-1-azetidinyl)-2-hyroxyacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

4-Ethylthio-3-p-nitrobenzyloxycarbonyloxyethyl-2-oxo-azetidine (9.0 g), p-nitrobenzyl glyoxylate ethyl hemiacetal (8.15 g) and benzene (350 ml) were heated at reflux for 20 hours under a nitrogen atmosphere using a Dean-Stark water separator. The solution was then concentrated in vacuo and the residue was dissolved in 700 ml of dichloromethane. The dichloromethane solution was washed two times with water, dried over anhydrous sodium sulfate and concentrated in vacuo to a yellowish semi-solid (15.0 g) of the title compound. The NMR spectrum in deuterochloroform showed peaks at 1.02-1.52 (c, 8H); 2.6 (m, 2H); 3.3 (m, 1H); 4.1 (b, 1H); 4.78-5.56 (c, 5H); 7.48 (d, 4H); and 8.18 (d, 4H) ppm. The IR spectrum in dichloromethane showed absorptions at 5.62 and 5.7 microns.

Aufarbeitung

  1. temperatureat reflux for 20 hours under a nitrogen atmosphere
  2. concentrationThe solution was then concentrated in vacuo
  3. dissolutionthe residue was dissolved in 700 ml of dichloromethane
  4. washThe dichloromethane solution was washed two times with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo to a yellowish semi-solid (15.0 g) of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-1167dc1b47d0476ebab7dc0c6dfdbd22
Quelldatensatz
uspto-grants-1986_10
Patentnummer
US04619783

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