Acetic Anhydride → (3R,4S,5R,6R)-6-(acetoxymethyl)-2-(3-((5-(4-fluorophenyl)thiophen-2-yl)methyl)-4-methylphenyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triyl

온도

0 °C

To a stirred solution of methyl 1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucopyranoside (net weight 10.54 g) in toluene and ethyl acetate was added N-methylmorpholine (11.9 g) and 4-dimethylaminopyridine (217 mg) at room temperature. The solution was cooled to 0° C. and acetic anhydride (52.7 mL) was added dropwise below 15° C. The reaction mixture was allowed to warm to room temperature and stirred for 15 hours. The mixture was quenched with 28% NH3 aqueous solution (ca. 31.6 mL) while maintaining pH range of 6 to 7. Water was added to the mixture and separated. The organic layer was washed with water and brine, dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in vacuo to give methyl 2,3,4,6-tetra-O-acetyl-1-C-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucopyranoside (17.59 g) as yellow oil.

1. temperatureto warm to room temperature
2. customThe mixture was quenched with 28% NH3 aqueous solution (ca. 31.6 mL)
3. temperaturewhile maintaining pH range of 6 to 7
4. additionWater was added to the mixture
5. customseparated
6. washThe organic layer was washed with water and brine
7. dry with materialdried over anhydrous MgSO4
8. filtrationfiltered
9. concentrationThe filtrate was concentrated in vacuo

ORD 기록

ord-bd5555f8abf44beabf098562749ed52b

출처 데이터셋

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09056850B2