1,1'-Carbonyldiimidazole → Methyl 2-((S)-(3-chlorophenyl)((R)-4-((2S,3R)-3-hydroxy-4-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-1-(tetrahydro-2H-pyran-4-yl)butan-2-ylcarbamoyl)morpholin-2-yl)methoxy)ethylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(trimethylsilyl)ethyl (2R,3S)-3-amino-2-hydroxy-4-(tetrahydro-2H-pyran-4-yl)butyl(methyl)carbamate (50 mg, 0.12 mmol) and CDI (20 mg, 0.12 mmol) in anhydrous CH2Cl2 (10 mL) cooled in an ice bath, DIEA (78 mg, 0.6 mmol) was added. After addition, the mixture was stirred for 1 h at 0° C. and added to a solution of methyl 2-((S)-(3-chlorophenyl)((R)-morpholin-2-yl)methoxy)ethylcarbamate (59 mg, 0.18 mmol) in anhydrous CH2Cl2 (2 mL). The reaction mixture was allowed to warm to rt and stirred overnight. After the reaction was complete, the solvent was removed in vacuo. The product was purified by preparative tlc to afford the desired product (30 mg, 36%).

Provenance & Evidence