Methyl N-(triethylammoniosulfonyl)carbamate → (S)-tert-butyl 4-(1-cyano-2-(4'-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate

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Reaction Steps

The mixture of (S)-tert-butyl 4-(1-amino-1-oxo-3-(4′-(trifluoromethyl)biphenyl-4-yl)propan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate and (S)-tert-butyl 4-(1-amino-3-(4′-(ethylsulfonyl)biphenyl-4-yl)-1-oxopropan-2-ylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (Example 1, step (iv), 1.7 g) in dichloromethane (15 mL) was treated with Burgess' reagent (1.19 g) and the mixture was stirred at room temperature for 72 h. The reaction was evaporated onto silica and purified on a silica column eluting with 20% ethyl acetate in isohexane, then 50% ethyl acetate in isohexane and finally 100% ethyl acetate to afford after evaporation of the relevant fractions (S)-tert-butyl 4-(1-cyano-2-(4′-(trifluoromethyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (650 mg) and (S)-tert-butyl 4-(1-cyano-2-(4′-(ethylsulfonyl)biphenyl-4-yl)ethylcarbamoyl)tetrahydro-2H-pyran-4-ylcarbamate (920 mg).

Provenance & Evidence