Water → t-butyl [N-(t-butoxycarbonyl)-N-(methoxycarbonyl)aminomethyl]-3-nitrobenzoate

반응식

BrC[C:3]1[CH:15]=[CH:14][C:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[CH:5][C:4]=1[N+:16]([O-:18])=[O:17].[NH:19]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:20]([O:22][CH3:23])=[O:21].[K].O.[CH3:33]N(C=O)C>>[C:27]([O:26][C:24]([N:19]([CH2:33][C:5]1[C:4]([N+:16]([O-:18])=[O:17])=[CH:3][CH:15]=[CH:14][C:6]=1[C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C:20]([O:22][CH3:23])=[O:21])=[O:25])([CH3:30])([CH3:29])[CH3:28]

참가 물질

반응물 4

HCID 962Water

HCID 6228Dimethylformamide2회

HCID 18462578t-Butyl 4-bromomethyl-3-nitrobenzoate

HCID 86754983Potassium t-butyl methyl iminodicarboxylate

생성물 1

HCID 86758139t-butyl [N-(t-butoxycarbonyl)-N-(methoxycarbonyl)aminomethyl]-3-nitrobenzoate수율 73%

실험 절차

To a solution of t-butyl 4-bromomethyl-3-nitrobenzoate (2.27 g, 7.2 mmol) (Int. J. Peptide Res., 36, 31 (1990)) in DMF (25 mL) was added a suspension of potassium t-butyl methyl iminodicarboxylate (J.C.S. Perkin I, 1088, (1977)) (1.56 g, 7.3 mmol) in DMF (20 mL). The dark brown solution was stirred 1 h and poured into water and extracted with ethyl acetate. The combined organic layers were washed with water, dried (sodium sulfate) and concentrated to give a pale orange oil which was purified by flash chromatography (silica gel, 20% ethyl acetate/hexane) to give the title compound (2.15 g, 73%). 1H NMR (400 MHz, CDCl3) δ8.65 (s, 1H), 8.2 (d, 1H), 7.45 (d, 1H), 5.3 (s, 2H), 3.8 (s, 3H), 1.6 (s, 9H), 1.45 (s, 9H).