3-Phenoxybenzoyl chloride → 18-(3-Phenoxybenzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene

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Reaction Steps

Prepared by way of method I using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo[14.3.0.04,6]-nonadec-7-ene (100 mg, 0.175 mmol) and 3-phenoxybenzoyl chloride (122 μL, 0.53 mmol). The final trituration (diethyl ether/hexane) and filtration gave 21 mg (16%) of 18-(3-phenoxybenzoyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-12-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 98.0% pure (HPLC), MS m/z 765 (M−H)−, HRMS: calcd. 767.2962 and found 767.2971 (M+H)+, mp 123-125° C.

Provenance & Evidence