Ethyl 2-((tert-butoxycarbonyl)amino)-1,3-thiazole-4-carboxylate → (4-Hydroxymethylthiazol-2-yl)carbamic acid tert-butyl ester

Temperature

-45 °C

Ethyl 2-(tert-butoxycarbonylamino)thiazole-4-carboxylate 88 (10.5 g, 38.6 mmol) was dissolved in 300 mL of anhydrous THF and cooled in dry ice-acetonitrile bath. A solution of 1 M Super Hydride™ in THF (85 mL) was then added over a period of 10 min. The resulting reaction mixture was stirred at −45° C. for 2 h. Another portion of 1 M Super Hydride™ in THF (35 mL) was then added and the reaction mixture was stirred for an additional 2 h at −45° C. The reaction was quenched at −45° C. by the addition of 50 mL of brine. Upon warming to room temperature, the reaction mixture was concentrated under reduced pressure. The resulting mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried with Na2SO4, and concentrated under reduced pressure. The resulting residue was purified by chromatography to afford 89 (6.39 g, 72% yield).

1. customThe resulting reaction mixture
2. stirringthe reaction mixture was stirred for an additional 2 h at −45° C
3. customThe reaction was quenched at −45° C. by the addition of 50 mL of brine
4. temperatureUpon warming to room temperature
5. concentrationthe reaction mixture was concentrated under reduced pressure
6. extractionThe resulting mixture was extracted with EtOAc
7. washThe combined organic layers were washed with brine
8. dry with materialdried with Na2SO4
9. concentrationconcentrated under reduced pressure
10. customThe resulting residue was purified by chromatography

ORD record

ord-10a357909e524ca49f2be272cb2ef0ee

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09326986B2