4-Phenylbenzoyl chloride → 18-(4-Biphenylcarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene

Participants

Reaction Steps

Prepared by way of method I using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo[14.3.0.04,6]-nonadec-7-ene (100 mg, 0.175 mmol) and 4-biphenylcarbonyl chloride (113 mg, 0.53 mmol). The final trituration (diethyl ether/hexane) and filtration gave 35 mg (27%) of 18-(4-biphenylcarbonyloxy)-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 98.9% pure (HPLC), MS m/z 749 (M−H)−, HRMS: calcd. 751.3013 and found 751.3008 (M+H)+, mp 160-162° C.

Provenance & Evidence