Acetamidomalonic acid diethyl ester → HCID 10501146、化合物
反応式
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].CC(C)([O-])C.[K+].Br[CH2:23][C:24]1[C:25]([O:34][CH3:35])=[N:26][O:27][C:28]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30]>CN1CCCC1=O>[C:1]([NH:4][C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])([CH2:23][C:24]1[C:25]([O:34][CH3:35])=[N:26][O:27][C:28]=1[C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]参加物
5
実験手順
A mixture of diethyl acetamidomalonate (1.6 g, 7.4 mmol) and potassium tert-butoxide (0.9 g, 8.0 mmol) in N-methylpyrrolidone (30 mL) was stirred at room temperature for 30 min. Ethyl 4-(bromomethyl)-3-methoxyisoxazole-5-carboxylate (1.8 g, 6.8 mmol) in N-methylpyrrolidone (10 mL) was added (temp 22-28° C.) and the resulting mixture was stirred at room temperature for 1.5 h. The reaction mixture was poured onto an ice/water mixture (100 mL) and the aqueous phase was extracted with EtOAc (3×150 mL). The organic extracts were washed with an aqueous solution of potassium tert-butoxide, water (100 mL) and brine (100 mL), dried (MgSO4) and concentrated in vacuo. Flash chromatography (silica gel, eluent: EtOAc/heptane=1:1) afforded crude title compound (1.8 g, 66%). A small sample was recrystallized (EtOAc/heptane) to give colourless crystals: mp 78-80° C. The crude product was used in the next step without further purification.