Hydrochloric Acid → HCID 67288735, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,6S,14aR,16aS,Z)-ethyl 6-(5-methylisoxazole-3-carboxamido)-2-(4-nitrobenzoyloxy)-5,16-dioxo-1,2,3,5,6,7,8,9,10,11,13a,14,14a,15,16,16a-hexadecahydrocyclopropa[e]pyrrolo[1,2-a][1,4]diazacyclopentadecine-14a-carboxylate (64.6 g solution, 15.5% w/w solution in THF, 10 g starting material) was added THF (34 mL). The solution was then cooled to 0° C. and a solution of 0.5M LiOH (33.8 mL) was added dropwise keeping the temperature below 5° C. After 1 hour, the reaction was diluted with dichloromethane (150 mL) and neutralized with 1N HCl (50 mL). The organic layer was extracted and washed with 5% NaHCO3 (50 mL) twice and once with a 5% aq. NaCl solution (50 mL). The dichloromethane layer was evaporated under reduced pressure and diluted with THF (41 g) to give a solution. Analysis by HPLC indicated a yield of 7.8 g of the title compound (100%).

Provenance & Evidence