Lithium Hydroxide → HCID 67288287, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2R,6S,14aR,16aS,Z)-ethyl 2-hydroxy-6-(5-methylisoxazole-3-carboxamido)-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 (10 g) in THF (52 g) and methanol (33 mL) at 0° C. was added 10% aq. LiOH (14.3 g). The solution was stirred at 10° C. for 22 h, then diluted with dichloromethane (150 mL). The reaction mixture was extracted with 1N HCl (100 mL) followed by water (100 mL). The solvent was changed to acetonitrile by distillation and the product crystallized. The final acetonitrile level was approximately 70 mL. The slurry was heated to 50° C. for 4 h, then allowed to cool to ambient temperature for 12 h. The slurry was filtered and the cake was washed with acetonitrile (20 mL) then dried under vacuum at 50° C. (8.5 g, 86% pure, 77% yield).

Provenance & Evidence