Water → HCID 19032033, compound

Temperature

0 °C

In a 100 mL round bottom flask equipped with a magnetic stirrer, N-Cbz phenyl glycinol (1.3 g, 5.0 mmol) was disssolved in CC14 (100 mL)and acetonitrile (100 mL). To this above solution was added water (15 mL) and periodic acid (4.7 g, 20.1 mmol, 4.1 eq). The reaction mixture was stirred until both phases became clear, then Ruthenium trichoride hydrate (0.025 g, 2.2 mol %). The reaction mixture was stirred at room temperature for 20 min and cooled to 0° C. then methylene cloride (30 mL) was added. The two phases were separated, the aqueous phase was extracted with chloroform (3×20 mL). The combined organic extracts were dried over (Na2SO4) and concentrated to afford the crud product. Flash chromatograpy (SiO2, 5×25 cm, 2-5% CH3OH—CHCl3 gradient elution) afforded pure pure N-Cbz phenyl glycine (1.2 g, 85%). Same Oxidation procedure was followed for compounds 1 and 2. No epimerization was observed during oxidation procedure.

1. customIn a 100 mL round bottom flask equipped with a magnetic stirrer
2. stirringThe reaction mixture was stirred at room temperature for 20 min
3. customThe two phases were separated
4. extractionthe aqueous phase was extracted with chloroform (3×20 mL)
5. dry with materialThe combined organic extracts were dried over (Na2SO4)
6. concentrationconcentrated
7. customto afford the crud product
8. washFlash chromatograpy (SiO2, 5×25 cm, 2-5% CH3OH—CHCl3 gradient elution)

ORD record

ord-8c45d616f0fe450f88c0e580a846158c

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06509506B1