Acetic Acid → Methyl bis(4-methylphenyl)azidoacetate

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Sodium bistrimethylsilylamide (1M solution in tetrahydrofuran, 9.82 ml) was added to a solution of methyl bis(4-methylphenyl)acetate (2.08 g, 8.18 mmol) dissolved in tetrahydrofuran(10 mL) and cooled to −78° C. under a nitrogen atmosphere. The reaction was stirred for 2.5 hours and then a solution of 2,4,6-triisopropylbenzenesulfonyl azide (2.78 g, 9 mmol) in tetrahydrofuran(6 mL) was added. This mixture was stirred for 45 minutes and then warmed to room temperature and stirred for an additional two hours. Glacial acetic acid (1.5 ml) was added and the mixture was stirred for 30 minutes. The reaction was diluted with diethyl ether and washed with saturated sodium bicarbonate and brine. The organic layer was dried over sodium sulfate, filtered and concentrated to afford crude product. This material was chromatographed on a column of silica gel eluting with 10% ethyl acetate/hexane to give the purified title compound as an oil which was used as is.

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