Hydrochloric Acid → HCID 11475547, compound

Participants

Reaction Conditions

Reaction Steps

Hydroxylamine hydrochloride (2.34 g, 33.7 mmol) was dissolved in methanol (12 mL) at 45° C. for 10 min in a 50 mL round bottom flask. B) Potassium hydroxyde (2.81 g, 50.0 mmol) was dissolved in methanol (7 mL) at 45° C. for 10 min in 25 mL round bottom flask. The solution B) was added in A) at 45° C. This mixture was stirred at 45° C. for 10 min and cooled to RT. The mixture was filtered and 5 mL of the filtrate were added at RT via syringe to a solution of ethyl 2-(4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)phenyl)-2,2-difluoroacetate 23 (0.10 g, 0.23 mmol) in methanol (4 mL). This mixture was stirred for 16 h at RT. A solution of HCl 1M was added to about pH=5. The aqueous layer was extracted with ethyl acetate (3×50 mL). The organic layer was dried over MgSO4, filtered and evaporated in vacuo. N-(4-((Hydroxycarbamoyl)difluoromethyl)phenyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamide EHT 4996 was obtained (123 mg, 97% yield) as an orange solid.

Provenance & Evidence