[NH:1]([CH:3]([CH2:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH:4]([OH:6])[CH3:5])[NH2:2].C(N(CC)CC)C.[CH3:23][O:24][C:25](OC)=[C:26]([C:29]#[N:30])[C:27]#[N:28]>CO.C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>[NH2:30][C:29]1[N:1]([CH:3]([CH2:7][CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:4]([OH:6])[CH3:5])[N:2]=[C:25]([O:24][CH3:23])[C:26]=1[C:27]#[N:28]
4.2 g of 3-hydrazino-2-hydroxy-6-phenylhexane are are dissolved in 20 ml of methanol, and 1.38 ml of triethylamine are added. Then, 1.38 g of 1,1-dimethoxy-2,2-dicyano-ethylene are added. The reaction solution is stirred for 2 hours at approx. 20° C. For work-up, the mixture is diluted with citric acid solution and ethyl acetate and extracted three times with ethyl acetate. The combined ethyl acetate phases are dried with magnesium sulphate and evaporated in vacuo. The evaporation residue is chromatographed on silica gel (Merck Si 60 0.04-0.063 mm) with a cyclohexane/ethyl acetate mixture in a ratio of 4:1 to 1:1. This gives a fraction which, after evaporation in vacuo, affords 0.959 g (=30.5% of theory) of 5-amino-4-cyano-3-methoxy-1-[2-hydroxy-6-phenyl-hex-3-yl]-pyrazole as diastereomer mixture.
読み込み中…
