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. 2013 Sep 19;9:1899–1906. doi: 10.3762/bjoc.9.224

Scheme 2.

Scheme 2

Synthesis of N-alkyl 3-carboxamide tetramic acid. Reaction conditions: (a) 1. glycine methyl ester∙HCl (1.0 equiv), Et3N (1.2 equiv), MgSO4 (2.0 equiv), THF, rt. 2. NaBH4 (2.0 equiv), MeOH, rt; (b) ethyl malonyl chloride (1.05 equiv), Et3N (1.2 equiv), CH2Cl2, rt; (c) KOt-Bu (1.1 equiv), THF, reflux; (d) amine (1.0 equiv), toluene, reflux; (e) butyl chloroformate (1.2 equiv), DMAP (2.2 equiv), CH2Cl2, rt.