Sodium Bicarbonate → (1R,2S)-1-({(2S,4R)-1-[(1S)-1-((1S,2R)-2-Acetoxy-indan-1-ylcarbamoyl)-2,2-dimethyl-propylcarbamoyl]-4-hydroxy-pyrrolidine-2-carbonyl}-amino)-2-vinyl-cyclopropanecarboxylic acid ethyl ester

Participants

Reaction Steps

To a stirred solution of compound 89 (1.81 g) in acetonitrile at 0° C. solid NaHCO3 (800 mg) and p-nitrophenychlorocarbonate (1.2 g) was added. The slurry was taken up to ambient temperature and stirred for another 30 min. To this slurry a solution of compound 91 (1.6 g) in acetonitrile (5 mL) diisopropylethylamine (1 mL) was added. After 10 min the resulting mixture was concentrated, re-dissolved in ethyl acetate and washed with K2CO3 (aq) and then with 0.5 N HCl. Dried and concentrated which gave a >80% pure product by HPLC M+H+599.6

Provenance & Evidence