(R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate → tert-Butyl ((R)-(4'-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)-phenyl)piperidin-4-yl)methoxy)methyl hydrogen phosphate

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Nitrolotrimethanol (5.27 mg, 0.05 mmol) was added to a solution of di-tert-butyl ((R)-(4′-chlorobiphenyl-2-yl)(1-(4-(4-((R)-4-morpholino-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)phenylsulfonylcarbamoyl)phenyl)piperidin-4-yl)methoxy)methyl phosphate (EXAMPLE 27, 58.0 mg, 0.05 mmol) in acetone (1.8 ml) and 0.6 ml of pH7.2 buffer (Gibco, Dulbecco's Phosphate Buffered saline 1×). The resulting reaction mixture was stirred at 65° C. for 16 hours. Evaporation of the volatiles under reduced pressure gave a residue which was purified by reverse phase HPLC (Gilson column, eluting with 30→50% H2O with 10 mM NH4OAc/MeCN for 5 minutes) to provide the title product (0.017 g, yield: 19%).

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