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To a solution 13.45 mmol of sodium methoxide in 6 mL absolute methanol at 0° C. was added a solution of 717 mg (3.24 mmol) of tert-butyl 4-formylphenylcarbamate and 1.49 g (12.96 mmol) methylazidoacetate dissolved in 6 mL absolute methanol dropwise over 5 minutes. The mixture was stirred at 0° C. for 6 h, then partitioned between ethyl acetate and acetic acid until neutral. The organic phase was dried over magnesium sulfate, concentrated and purified by column chromatography, eluting with 25% ethyl acetate/hexane to provide 551 mg of methyl (2E)-2-azido-3-{4-[(tert-butoxycarbonyl)amino]phenyl}prop-2-enoate as a yellow solid.

1. custompartitioned between ethyl acetate and acetic acid until neutral
2. dry with materialThe organic phase was dried over magnesium sulfate
3. concentrationconcentrated
4. custompurified by column chromatography
5. washeluting with 25% ethyl acetate/hexane