Triethylamine → HCID 178501061, Verbindung

Reaktionsgleichung

[C:1](=[N:4][OH:5])([NH2:3])[CH3:2].C(N(CC)CC)C.[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23](Cl)=O)[CH2:19][CH2:18]1)=[O:16]>O1CCCC1>[CH3:13][O:14][C:15]([C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]2[O:5][N:4]=[C:1]([CH3:2])[N:3]=2)[CH2:19][CH2:18]1)=[O:16]

Komponenten

Versuchsvorschrift

To a solution of acetamide oxime (0.19 g, 2.6 mmol) and triethylamine (0.36 ml, 2.6 mmol) in tetrahydrofuran (24 ml) was added trans-4-chlorocarbonyl-cyclohexanecarboxylic acid methyl ester (0.50 g, 2.4 mmol) at 0-5° C. After completed addition the cooling bath was removed, and the mixture was stirred for 30 minutes. The precipitated ammonium salts were removed by filtration and washed with tetrahydrofuran. The filtrate was concentrated to dryness. The residue was redissolved in 1,4-dioxane (24 ml). The mixture was treated with a catalytic amount of toluene-4-sulfonic acid monohydrate and heated at reflux over night (16 h). The solvent was evaporated. Flash-chromatography with n-heptane/ethyl acetate as eluent gave the title compound (0.48 g, 88%) as light brown oil. MS m/e: 225 ([M+H]+)