tert-Butyldimethylsilyl chloride → (1r)-1-{[2(s)-(Hex-5-enyl-methyl-carbamoyl)-4(r)-tert-butyldimethylsilyloxy-pyrrolidine-n-carbonyl]-amino}-2(r)-vinyl-cyclopropanecarboxylic acid ethyl ester

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Reaction Steps

Under nitrogen atmosphere, the tert-butyldimethylsilyl chloride was added to a solution of compound 50 (750 mg, 1 eq.) and TEA (537 μL, 1 eq.) in DCM (6 mL). The reaction mixture was stirred overnight at room temperature and quenched with water. The organic layer was washed with brine, dried on sodium sulfate, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to yield compound 51 in 70% yield.

Provenance & Evidence