Potassium sodium tartarate → N-(4-{2-[5-(3-hydroxypropyl)thiophen-3-yl]ethyl}-1,3-thiazol-2-yl)acetamide

Temperature

-45 °C

To a solution of methyl 3-(4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}thiophen-2-yl)propionate (1.450 g, 4.284 mmol) in anhydrous tetrahydrofuran (28 ml) was added dropwise 1.5M diisobutylaluminum hydride (10.7 ml, 16.1 mmol) at −50° C. over 30 min. After stirring at −50 to −40° C. for 2 hr, saturated aqueous potassium sodium tartrate solution (60 ml) was added. The mixture was warmed to room temperature, and stirred for 1.5 hr. The mixture was extracted 3 times with ethyl acetate, and washed with 1M hydrochloric acid, saturated-aqueous sodium hydrogen carbonate and saturated brine. After drying over anhydrous magnesium sulfate, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g, ethyl acetate:hexane=2:1) to give N-(4-{2-[5-(3-hydroxypropyl)thiophen-3-yl]ethyl}-1,3-thiazol-2-yl)acetamide (499.9 mg, 1.610 mmol, yield 37.6%) as a white solid.

1. temperatureThe mixture was warmed to room temperature
2. stirringstirred for 1.5 hr
3. extractionThe mixture was extracted 3 times with ethyl acetate
4. washwashed with 1M hydrochloric acid, saturated-aqueous sodium hydrogen carbonate and saturated brine
5. dry with materialAfter drying over anhydrous magnesium sulfate
6. concentrationthe mixture was concentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 100 g, ethyl acetate:hexane=2:1)

ORD record

ord-d81ff6ba44a44df0bb0b61b0443d1727

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507690B2