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目的合成具有抗肿瘤活性和免疫调节作用的3-氨基-N-(2,6-二氧代-3-哌啶基)-邻苯二甲酰亚胺(pomalidomide,1)。方法 N-Boc-L-谷氨酰胺(2)经羰基二咪唑缩合、脱保护得到3-氨基哌啶-2,6-二酮盐酸盐(4);3-硝基邻苯二甲酸(5)环合得到3-硝基邻苯二甲酸酐(6);4与6在乙酸中缩合,再经甲酸铵/钯炭还原得到目标产物。结果与结论经过5步反应合成目标化合物,总收率为46.5%(以5计),目标化合物结构经1H-NMR和MS谱确证。
Objective To synthesize 3-amino-N- (2,6-dioxo-3-piperidinyl) -phthalimide (1) with anti-tumor activity and immunomodulatory effects. Methods N-Boc-L-glutamine (2) was condensed with carbonyldiimidazole to give 3-aminopiperidine-2,6-dione hydrochloride (4) 5) cyclization to give 3-nitro phthalic anhydride (6); 4 and 6 in acetic acid condensation, and then ammonium formate / palladium carbon reduction to give the desired product. Results and Conclusion After 5 steps, the target compound was synthesized and the total yield was 46.5% (calculated by 5). The structure of the target compound was confirmed by 1H-NMR and MS spectra.