Ethyl Acetate → [5-(3-Methyl-[1,2,4]oxadiazol-5-yl)-4-phenyl-thiazol-2-yl]-carbamic Acid tert-butyl ester

2-Tert-butoxycarbonylamino-4-phenyl-thiazole-5-carboxylic acid ethyl ester (1.9 g 5.6 mmol) was dissolved in dry THF (60 mL). Sodium hydride (60% in oil) and N-hydroxy-acetamidine (0.83 g, 11.2 mmol) dissolved in THF (30 mL) was added. The reaction mixture was heated to reflux over night. The reaction mixture was cooled and ethyl acetate (75 mL) glacial acetic acid (0.43 g) were added. The organic mixture was washed with brine (75 mL). The aqueous phase was extracted with ethylacetate The combined organic phases was washed with brine (50 mL) dried with MgSO4 and solvents were removed in vacuo to give a solid. Yield: 36%.

1. additionwas added
2. temperatureThe reaction mixture was heated
3. temperatureto reflux over night
4. temperatureThe reaction mixture was cooled
5. washThe organic mixture was washed with brine (75 mL)
6. extractionThe aqueous phase was extracted with ethylacetate The combined organic phases
7. washwas washed with brine (50 mL)
8. dry with materialdried with MgSO4 and solvents
9. customwere removed in vacuo
10. customto give a solid

ORD 기록

ord-1fc7453889f240fc94996d1a9dc9328a

출처 데이터셋

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07910613B2