Sodium hydride → 5-(4-methoxybutyl)-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid

A solution of sodium hydride (60% in oil, 2 g) in DMF (50 ml) was cooled to 0° C.-5° C., methyl 7-methoxy-3-oxoheptanoate (9.4 g) was added, and the mixture was stirred at 0° C.-5° C. for 30 min. Phenyl azide (6 g) was added, and the mixture was stirred at room temperature for 15 hr. The solvent was concentrated under reduced pressure, and methanol (100 ml) was added to the residue and 4N aqueous sodium hydroxide solution (20 ml) was further added. The mixture was stirred at 60° C. for 1 hr. The solvent was evaporated under reduced pressure and water (100 ml) was added to the residue. 6N Hydrochloric acid was added for neutralization and the mixture was extracted with ethyl acetate (100 ml×2). The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate was concentrated under reduced pressure to give the object product (7.2 g) as a white powder.

1. stirringthe mixture was stirred at room temperature for 15 hr
2. concentrationThe solvent was concentrated under reduced pressure, and methanol (100 ml)
3. additionwas added to the residue and 4N aqueous sodium hydroxide solution (20 ml)
4. additionwas further added
5. stirringThe mixture was stirred at 60° C. for 1 hr
6. customThe solvent was evaporated under reduced pressure and water (100 ml)
7. additionwas added to the residue
8. addition6N Hydrochloric acid was added for neutralization
9. extractionthe mixture was extracted with ethyl acetate (100 ml×2)
10. dry with materialThe extract was dried over anhydrous sodium sulfate
11. customthe solvent was evaporated under reduced pressure
12. washa fraction eluted with ethyl acetate
13. concentrationwas concentrated under reduced pressure

ORD record

ord-534234dd84574ee28b5e5d3b05e34b4d

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09221836B2