Cyclohexanecarbonyl chloride → 18-Cyclohexanecarbonyloxy-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 I of example 27 using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo[14.3.0.04,6]-nonadec-7-ene (50 mg, 0.088 mmol) and cyclohexanecarbonyl chloride (35 μL, 0.26 mmol). The final trituration (diethyl ether/petroleum ether) and filtration gave 16 mg (27%) of 18-cyclohexanecarbonyloxy-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: 96.1% pure (HPLC), MS m/z 679 (M−H)−, HRMS: calcd. 679.3013 and found 679.3007 (M−H)−, mp 128-130° C.

Provenance & Evidence