Hydrogen Peroxide → HCID 86726383, compound

Temperature

0 °C

To a solution of 3-[2-(S)-azido-3,3-bis-(4-chloro-phenyl)-propionyl]-4-(S)-benzyl-oxazolidin-2-one (1.53 g, 3.1 mmol) in 3:1 THF/water (60 mL) at 0° C. was added 30% aq. H2O2 (1.4 mL, 12.3 mmol) and LiOH.H2O (259 mg, 6.2 mmol). The mixture was stirred for 1 h at 0° C. Na2SO3 (2.52 g, 20 mmol) was added, and the mixture was stirred for 30 min at 0° C., then warmed to rt, and stirred for 1 h. The mixture was concentrated without external heating, and the residue was diluted with water and extracted with DCM (3×). The aqueous layer was acidified with conc. HCl and extracted with EtOAc (4×). The combined EtOAc extracts were dried (Na2SO4) and concentrated to provide the desired azidoacid as a colorless solid (0.98 g, 94%). 1H NMR (500 MHz, CDCl3): 7.33-7.24 (m, 6H), 7.21-7.18 (m, 2H), 4.52 (d, J=8.3, 1H), 4.49 (d, J=8.3, 1H).

1. stirringthe mixture was stirred for 30 min at 0° C.
2. temperaturewarmed to rt
3. stirringstirred for 1 h
4. concentrationThe mixture was concentrated without external heating
5. additionthe residue was diluted with water
6. extractionextracted with DCM (3×)
7. extractionextracted with EtOAc (4×)
8. dry with materialThe combined EtOAc extracts were dried (Na2SO4)
9. concentrationconcentrated

ORD record

ord-647327ff23a74eb9b12876ff1499d590

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855292B2