Phosphorus oxychloride → HCID 57811515, compound

Temperature

0 °C

Phosphorus oxychloride (2.4 mmol) is added dropwise over 5 mins to a solution of 2-(5-bromo-4-(1-cyclopropylnaphthalen-4-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid (810 mg, 2.0 mmol) in pyridine (20 mL) at 0° C. The mixture is stirred at 0° C. for a further 1 hour and then 1,2-O-isopropilydene-□-D-glucofuranose (440 mg, 2.0 mmol) dissolved in pyridine (5 mL) is added dropwise over 5 mins. The mixture is stirred at 0° C. for a further 3 hours and 1 hour at 20° C. and then quenched by addition of water (1 mL). Volatile solvents are removed in vacuo and DCM (200 mL) added. The organic phase is washed with water (1×50 mL), saturated sodium carbonate solution (1×50 mL) and brine (1×50 mL), dried over Na2SO4 and concentrated to dryness. Ethanol and water are added to produce a solid which is collected by filtration. Additional product is recovered by extraction of the filtrate with DCM. Combined product is concentrated, dried and purified by column chromatography (acetone/DCM eluent). The combined solids are dissolved in acetic acid (25 mL) and water (5 mL) mixture, heated at 60° C. for 3 hours. Volatile solvents are removed in vacuo. Ethanol and water are added to produce a solid which is collected by filtration.

1. additionis added dropwise over 5 mins
2. stirringThe mixture is stirred at 0° C. for a further 3 hours and 1 hour at 20° C.
3. customquenched by addition of water (1 mL)
4. customVolatile solvents are removed in vacuo and DCM (200 mL)
5. additionadded
6. washThe organic phase is washed with water (1×50 mL), saturated sodium carbonate solution (1×50 mL) and brine (1×50 mL)
7. dry with materialdried over Na2SO4
8. concentrationconcentrated to dryness
9. additionEthanol and water are added
10. customto produce a solid which
11. filtrationis collected by filtration
12. customAdditional product is recovered by extraction of the filtrate with DCM
13. concentrationCombined product is concentrated
14. customdried
15. custompurified by column chromatography (acetone/DCM eluent)
16. dissolutionThe combined solids are dissolved in acetic acid (25 mL)
17. temperaturewater (5 mL) mixture, heated at 60° C. for 3 hours
18. customVolatile solvents are removed in vacuo
19. additionEthanol and water are added
20. customto produce a solid which
21. filtrationis collected by filtration

ORD record

ord-a287587344334b159dd596629d4f00f9

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08084483B2