2,6-Lutidine → p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate

HRID 1982148

Reaktionsgleichung

Reaktionsgleichung von HRID 1982148
[CH2:1]([S:3][CH:4]1[N:7]([CH:8](O)[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:23])[CH2:5]1)[CH3:2].CC1C=CC=C(C)N=1.S(Cl)([Cl:34])=O>O1CCCC1>[CH2:1]([S:3][CH:4]1[N:7]([CH:8]([Cl:34])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:23])[CH2:5]1)[CH3:2]

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 24386Thionyl ChlorideHCID 14050377p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate

Produkt 1

HCID 14050378p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 6.8 g. of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate in 200 ml. of tetrahydrofuran at 0°-5° C. was added 2.98 ml. of 2,6-dimethylpyridine. This was followed by dropwise addition of a solution of 1.73 ml. of thionyl chloride in 20 ml. of tetrahydrofuran, over a 5-minute period. Stirring was continued at 0°-5° C. for 15 minutes, and then the reaction mixture was filtered. The filtrate was evaporated to dryness in vacuo, and the residue was dissolved in 200 ml. of dichloromethane. The resulting solution was washed successively with dilute hydrochloric acid and water, and dried with anhydrous sodium sulfate. Evaporation in vacuo gave the title compound as a yellow, viscous liquid (yield: 7.12 g). The IR spectrum (CHCl3) of the product showed an absorption at 5.63 microns. The NMR spectrum (CDCl3) of the product showed absorptions at 1.3(t,3H); 2.47-3.7(m,4H); 4.9-5.3(m, 1H); 5.4(s,4H); 6.06 and 6.18(ss,1H); 7.58 (d,2H); and 8.22(d,2H) ppm.

Aufarbeitung

  1. additionThis was followed by dropwise addition of a solution of 1.73 ml
  2. filtrationthe reaction mixture was filtered
  3. customThe filtrate was evaporated to dryness in vacuo
  4. dissolutionthe residue was dissolved in 200 ml
  5. washThe resulting solution was washed successively with dilute hydrochloric acid and water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customEvaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f85d09ea25f64a0d84ae2cf9c50939c0
Quelldatensatz
uspto-grants-1986_06
Patentnummer
US04595539

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