Toluene → Methyl 2-((tert-butoxycarbonyl)amino)prop-2-enoate

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Reaction Steps

A solution of N-(tert-butyloxycarbonyl)-DL-serine methyl ester {5.48 g, Reference Example 15(a)} in tetrahydrofuran (60 mL) was treated with triethylamine (3.48 mL) followed by carbonyldiilmidazole (4.05 g). The mixture was stirred at room temperature overnight and then evaporated. The residue was extracted several times with tert-butyl methyl ether. The combined extracts were evaporated to give a colourless oil which was subjected to flash chromatography on silica eluting with toluene to give the title compound (3.64 g) as a colourless oil.

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