Triethylamine → HCID 86627907, compound

Temperature

-78 °C

NEt3 was added to a stirred mixture of 4-azidobutanoic acid in THF (0.3 M) cooled to −78° C. and stirring was continued at this temperature for 10 min. Pivaloyl chloride (1.3 eq) was added dropwise. The resulting mixture was warmed to 0° C. and stirred for 1 h before re-cooling to −78° C. In a separate flask, (4S)-4-benzyl-1,3-oxazolidin-2-one was dissolved in THF (0.8 M) and cooled to −78° C. before dropwise addition of N-BuLi (1.6M, 1.35 eq.) over 10 min. The mixture was stirred at −78° C. for 1 h and then transferred into the −78° C. solution of mixed anhydride using a syringe. The reaction was stirred at −78° C. for 1 h, then at RT for a further 1 h. The reaction was quenched by addition of sat. aq. NH4Cl before partitioning between H2O and EtOAc. The layers were separated and the aqueous phase re-extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified by FC eluting with 10 to 30% EtOAc/PE to give the product as a colourless oil (74%). (ES+) m/z 289 (M+H)+.

1. temperatureThe resulting mixture was warmed to 0° C.
2. stirringstirred for 1 h
3. temperaturebefore re-cooling to −78° C
4. stirringThe mixture was stirred at −78° C. for 1 h
5. stirringThe reaction was stirred at −78° C. for 1 h
6. waitat RT for a further 1 h
7. customThe reaction was quenched by addition of sat. aq. NH4Cl
8. custombefore partitioning between H2O and EtOAc
9. customThe layers were separated
10. extractionthe aqueous phase re-extracted with EtOAc
11. washThe combined organic extracts were washed with brine
12. dry with materialdried over Na2SO4
13. filtrationfiltered
14. concentrationconcentrated in vacuo
15. customThe residue was purified by FC
16. washeluting with 10 to 30% EtOAc/PE

ORD record

ord-b9da903cf4864a0989f373b8883bad0f

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07989438B2