Acetone → HCID 54557443, compound

HRID 1710233Notes

Reaction equation

HRID 1710233 reaction equation
[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]

Participants

6

Reactant 4

HCID 180AcetoneHCID 1115963335444-20-3HCID 14263577HCID 14263577, compoundHCID 21584019Toluene ethylacetate

Product 1

HCID 54557443HCID 54557443, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7c04ecce676245b5971aab88bdebed49
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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