[C:1]1([C@@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN1CC[O:19]CC1.ClC(OCC(C)C)=O.C(N1[C:40]([NH2:41])=[C:39]([NH2:42])[C:37](=[O:38])N(CC=C)C1=O)C=C>O1CCCC1.C(OCC)C>[C:1]1([C@@H:7]2[CH2:11][CH2:10][CH2:9][C@H:8]2[C:12]([OH:14])=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:1]([CH:7]1[C:11](=[O:19])[CH:10]([CH2:9][CH:8]=[CH2:12])[C:37](=[O:38])[C:39]([NH-:42])=[C:40]1[NH2:41])[CH:2]=[CH2:3]Dissolve trans-2-phenyl-cyclopentanecarboxylic acid (1.0 g, 5.3 mmol), prepared according to F. G. Bordwell and J. Almy, J. Org. Chem., 38, 571 (1973), in tetrahydrofuran (20 ml) and add N-methylmorpholine (0.58 ml, 5.3 mmol). Cool the reaction to -20° C. and add isobutyl chloroformate (0.69 ml, 5.3 mmol). Stir the reaction for 30 minutes, add 1,3-diallyl-5,6-diaminouracil (1.2 g, 5.3 mmol, in 4 ml dimethylformamide) and stir at -20° C. for 3 hours. Warm to room temperature and dilute the reaction with diethyl ether (400 ml). Separate the layers and rinse the organic layer with saturated sodium bicarbonate (2×200 ml), 50% aqueous sodium chloride (2×300 ml), dry over anhydrous magnesium sulfate, filter and concentrate under vacuum. Purify the residue by radial chromatography (2% to 5% methanol/chloroform, 2 mm plate) to provide trans-2-phenyl-cyclo-pentanecarboxylic acid (3,5-diallyl-2-amino-4,6-dioxo-cyclohex-1-enylamide (0.51 g).
読み込み中…
