Oxazolo(4,5-b)pyridine → (S)-[1-(hydroxy-oxazolo[4,5-b]pyridin-2-yl-methyl)-propyl]-carbamic acid tert-butyl ester

温度

0 °C

In a clean roundbottom flask equipped with stir bar was placed oxazolo[4,5-b]pyridine (600 mg, 5 mmol) in THF (30 mL) and the reaction mixture was cooled to 0° C. under N2 atomosphere. Isopropylmagnesium chloride (2 M in THF, 2.5 mL, 5 mmol) was added. After stirring for 1 h at 0° C., (S)-2-(tert-butoxycarbonyl)aminobutyraldehyde (573 mg, 3 mmol) in THF (20 mL) was added. The ice bath was removed and the reaction mixture was allowed to warm to room temperature. After 2 h, the reaction mixture was quenched with saturated ammonium chloride solution and concentrated to dryness. The residue was extracted with EtOAc, then washed with brine, dried with anhyd. MgSO4, filtered and concentrated. The crude product was purified by chromatograph to yield 383 mg of the desired compound.

1. customIn a clean roundbottom flask equipped
2. stirringAfter stirring for 1 h at 0° C.
3. customThe ice bath was removed
4. temperatureto warm to room temperature
5. customthe reaction mixture was quenched with saturated ammonium chloride solution
6. concentrationconcentrated to dryness
7. extractionThe residue was extracted with EtOAc
8. washwashed with brine
9. customdried with anhyd
10. filtrationMgSO4, filtered
11. concentrationconcentrated
12. customThe crude product was purified by chromatograph

ORDレコード

ord-31ea632856d34325b982e711efca3ec7

出典データセット

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07101880B2