1,8-Diazabicyclo(5.4.0)undec-7-ene → tert-butyl N-[(3S,3aR,6R,6aR)-3-[[6-chloro-5-(4-phenylphenyl)-1-(2-trimethylsilylethoxymethyl)imidazo[4,5-b]pyridin-2-yl]amino]-2,3,3a,5,6,6a-hexahydrofuro[3,2-b]furan-6-yl]carbamate

Participants

Reaction Steps

DBU (18.3 uL, 0.122 mmol) was added to a mixture of 2-[[6-chloro-2-methylsulfonyl-5-(4-phenylphenyl)imidazo[4,5-b]pyridin-1-yl]methoxy]ethyl-trimethyl-silane (50 mg, 0.097 mmol) and tert-butyl N-[(3S,3aR,6R,6aR)-3-amino-2,3,3a,5,6,6a-hexahydrofuro-[3,2-b]furan-6-yl]carbamate (72.6 mg, 0.297 mmol) in DMF (0.39 mL). After 18 hours, the mixture was diluted with ethyl acetate (20 mL) and washed with water (5×20 mL). The organic layer was separate, washed with brine (1×10 mL), dried with MgSO4, filtered and the solvent was removed under vacuum. The crude reaction mixture was then purified on preparative silica gel plates (1×1000 u—developed with 30% EtOAc/hexanes and eluted with EtOAc) to give the title compound. LC-MS: calculated for C35H44ClN5O5Si 677.28 observed m/e minor isomer 678.31 (M+H)+ (Rt 1.34/2 min) and major isomer 608.23 (M+H)+ (Rt 1.04/2 min)

Provenance & Evidence