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

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Reaction Steps

Prepared by way of method III 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 2-carbomethoxyphenyl isocyanate (62 mg, 0.35 mmol). The final trituration (diethyl ether/hexane) and filtration gave 53 mg (41%) of 18-(2-carbomethoxyphenylaminocarbonyloxy)-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: 99.6% pure (HPLC), MS m/z 746 (M−H)−, HRMS: calcd. 786.2423 and found 786.2436 (M−H+K)−, mp 147-149° C.

Provenance & Evidence