Trifluoroacetic acid → [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol

[(3S,4S,5R,6S)-3,4,5-tribenzyloxy-6-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-2-yl]methanol 2n (500 mg, 0.66 mmol) was dissolved in 10 mL dichloromethane, followed by dropwise addition of trifluoroacetic acid (0.2 mL, 2.62 mmol). The reaction mixture was stirred for 1.5 hours. Thereafter, the reaction mixture was washed with 10 mL saturated sodium bicarbonate solution and the organic extract was combined, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by silica gel chromatography with elution system B to obtain the title compound [(1S,2S,3S,4R,5S)-2,3,4-tribenzyloxy-5-[4-chloro-3-[(2,3-difluoro-4-methoxy-phenyl)methyl]phenyl]-6,8-dioxabicyclo[3.2.1]octan-1-yl]methanol 2p (360 mg, white solid), with yield: 75.3%. MS m/z (ESI): 746.2 [M+18].

1. washThereafter, the reaction mixture was washed with 10 mL saturated sodium bicarbonate solution
2. extractionthe organic extract
3. dry with materialdried over anhydrous magnesium sulfate
4. filtrationfiltered
5. concentrationThe filtrate was concentrated under reduced pressure
6. customthe resulting residue was purified by silica gel chromatography with elution system B

ORD record

ord-4d5cd2980c8147f5b9e708b1dc200639

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609622B2