Acetone → HCID 54557443, Verbindung

HRID 1710233Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710233
[C:1](=[S:6])([S-:5])[S:2][CH2:3][CH3:4].[K+].C(O[CH:12]1[NH:15][C:14](=[O:16])[CH:13]1[CH:17]([CH3:19])[CH3:18])(=O)C.CC(C)=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>O>[CH2:3]([S:2][C:1]([S:5][CH:12]1[NH:15][C:14](=[O:16])[CH:13]1[CH:17]([CH3:19])[CH3:18])=[S:6])[CH3:4]

Komponenten

6

Edukt 4

HCID 180AcetoneHCID 11159633potassium ethyl trithiocarbonateHCID 14263577HCID 14263577, VerbindungHCID 21584019Toluene ethylacetate

Produkt 1

HCID 54557443HCID 54557443, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

A solution of 230 mg of potassium ethyl trithiocarbonate in 1.5 ml of water is added dropwise at room temperature, in a nitrogen atmosphere, to a solution of 195 mg (1.14 mmole) of 4-acetoxy-3-isopropylazetidin-2-one (racemic mixture of cis- and trans-isomer in the ratio of 1:3) in 1 ml of water and 0.2 ml of acetone and the mixture is stirred at the same temperature for 120 minutes. The reaction mixture is exhaustively extracted with methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo. The residue is chromatographed over 12 g of silica gel with toluene/ethyl acetate (9:1) and yields the trans-title compound. Melting point: 65°-66° TLC: Rf =0.5 (toluene/ethyl acetate 2:3]; IR spectrum (CH2Cl2): absorption bands at 2.95, 3.37, 5.62 and 9.25μ. NMR spectrum (in CDCl3 /100 Mc, in ppm): 6.65, 1H, m (exchange with D2O); 5.4, 1 H, d (J=2.5 Hz): 3.39, 2H, q; 3.05, 1H, m; 2.15, 1H, m: 1.38, 3H, t; 1.1, 6H, m.

Aufarbeitung

  1. extractionThe reaction mixture is exhaustively extracted with methylene chloride
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated by evaporation in vacuo
  4. customThe residue is chromatographed over 12 g of silica gel with toluene/ethyl acetate (9:1)
  5. customyields the trans-title compound
  6. customIR spectrum (CH2Cl2): absorption bands at 2.95, 3.37, 5.62 and 9.25μ

Quellen und Nachweise

ORD-Eintrag
ord-7c04ecce676245b5971aab88bdebed49
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04952690

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