Triethylamine → t-butyl N-[5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)-2-[4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetylamino]phenyl]-N-methylcarbamate

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Reaction Steps

A mixture of t-butyl N-[2-amino-5-(4-t-butoxycarbonylamino-3,5-dimethylphenoxy)phenyl]-N-methylcarbamate (1.56 g), 4-(2,4-dioxothiazolidin-5-ylmethyl)phenoxyacetic acid (1.05 g), diethyl cyanophosphonate (0.61 g), triethylamine (0.38 g) and anhydrous tetrahydrofuran (30 ml) was stirred at room temperature for 19 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The extract was dried over anhydrous sodium sulfate and concentrated. The residue was chromatographed on a silica gel column using ethyl acetate:n-hexane=1:1 as the eluant to afford the desired compound (1.89 g, Rf=0.19: thin layer chromatography on a silica gel plate using ethyl acetate:n-hexane=2:3 as the eluant).

Provenance & Evidence