Tetrahydrofuran → (S)-ethyl 1-((S)-2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidine-3-carboxylate

5-Phenyl-4-(trifluoromethyl)isoxazole-3-carbonyl fluoride, Int-II-D (78 mg, 0.3 mmol) was dissolved in acetonitrile (5 mL) and (S)-ethyl 1-((S)-2-hydroxy-2-(4-((Z)—N′-hydroxycarbamimidoyl)phenyl)ethyl)piperidine-3-carboxylate, Preparation 14B (100 mg, 0.298 mmol) was added. After 2 hours, 1M TBAF in THF (298 μL, 0.298 mmol) was added and the reaction mixture was stirred overnight. The reaction mixture was diluted with ethyl acetate and washed with H2O. The organic layer was dried with MgSO4, filtered, and concentrated. The resulting material was purified on a silica gel cartridge using an EtOAc/hexanes gradient to yield 67 mg of (S)-ethyl 1-((S)-2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)ethyl)piperidine-3-carboxylate. MS (m+1)=557. HPLC Peak RT=3.32 minutes (Analytical Method A).

1. additionwas added
2. washwashed with H2O
3. dry with materialThe organic layer was dried with MgSO4
4. filtrationfiltered
5. concentrationconcentrated
6. customThe resulting material was purified on a silica gel cartridge

ORD record

ord-b8f39694d9be431d9dc45ce3d66d08ee

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399451B2