Acetone → HCID 54557443、化合物

HRID 1710233ノート

反応式

HRID 1710233 の反応式
[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]

参加物

6

反応物 4

HCID 180AcetoneHCID 11159633potassium ethyl trithiocarbonateHCID 14263577HCID 14263577、化合物HCID 21584019Toluene ethylacetate

生成物 1

HCID 54557443HCID 54557443、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7c04ecce676245b5971aab88bdebed49
出典データセット
uspto-grants-1990_08
特許番号
US04952690

反応ノート

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