Tetrahydrofuran → Diphenyl phosphite

and triflate 13 isomer B (115 mg, 0.274 mmol) in THF (2 mL) was added Cs2CO3 (119 mg, 0.366 mmol). After the reaction mixture was stirred for 30 min at room temperature, the mixture was partitioned between EtOAc and water. The organic phase was dried over Na2SO4, filtered, and evaporated under reduced pressure. The crude product was chromatographed on silica gel (eluting 60-80% EtOAc/hexane) to give a mixture. The mixture was further purified by HPLC on C18 reverse phase chromatography (eluting 55% CH3CN/water) to give phosphonate 14 isomer B (28 mg, 18%) as a colorless solid. 1H NMR (300 MHz, CDCl3) δ 7.71 (d, 2H), 7.26 (m, 6H), 6.94 (m, 5H), 5.66 (d, 1H), 5.17 (m, 1H), 4.99 (m, 2H), 4.55 (m, 1H), 4.42 (m, 1H), 4.16 (m, 2H), 3.97 (m, 1H), 3.85 (m, 5H), 3.72 (m, 3H), 3.13 (m, 1H), 2.97 (m, 4H), 2.80 (m, 2H), 1.83 (m, 1H), 1.60 (m, 6H), 1.22 (m, 3H), 0.93 (d, 3H), 0.88 (d, 3H). 31P NMR (300 MHz, CDCl3) δ 15.3. Resolution of Compound 14 Diastereomers

1. customthe mixture was partitioned between EtOAc and water
2. dry with materialThe organic phase was dried over Na2SO4
3. filtrationfiltered
4. customevaporated under reduced pressure
5. customThe crude product was chromatographed on silica gel (eluting 60-80% EtOAc/hexane)
6. customto give a mixture
7. customThe mixture was further purified by HPLC on C18 reverse phase chromatography (eluting 55% CH3CN/water)

ORD record

ord-8be7d9cc514e492eada4aeba7db01280

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07649015B2