Sodium Azide → Methyl 2-azido-3-(benzylsulfanyl)propanoate

Following a method described by Aubé and coworkers [S. K. Ramanathan, J. Keeler, H.-L. Lee, D. S. Reddy, G. Lushington, J. Aubé, Org. Lett. 2005, 7, 1059-1062], a solution of NaN3 (0.88 g, 13.7 mmol) in H2O (2.5 mL) was cooled to 0° C. and CH2Cl2 (4 mL) was added. Whilst the mixture was stirring vigorously, Tf2O (CF3SO2OSO2CF3, 0.47 mL, 2.26 mmol) was added dropwise. The resulting solution was stirred for an additional 2 h. The mixture was then placed in a separating funnel, and the organic layer was removed. The aqueous phase was extracted further with CH2Cl2 (2×3 mL). The organic layers were combined, washed with saturated Na2CO3, dried over Na2SO4(s), and filtered. The resulting solution of TfN3 was added dropwise to a solution of methyl 2-amino-3-(benzylsulfanyl)propanoate hydrochloride salt (0.37 g, 1.40 mmol) and DMAP (0.75 g, 6.16 mmol) in CH2Cl2 (5 mL). The resulting solution was stirred overnight under Ar(g). The mixture was concentrated under reduced pressure and purified by silica gel flash chromatography, eluting with CH2Cl2, to give azide 2e as an oil (0.26 g, 1.05 mmol, 75% yield).

1. stirringThe resulting solution was stirred for an additional 2 h
2. customThe mixture was then placed in a separating funnel
3. customthe organic layer was removed
4. extractionThe aqueous phase was extracted further with CH2Cl2 (2×3 mL)
5. washwashed with saturated Na2CO3
6. dry with materialdried over Na2SO4(s)
7. filtrationfiltered
8. concentrationThe mixture was concentrated under reduced pressure
9. custompurified by silica gel flash chromatography
10. washeluting with CH2Cl2

ORD record

ord-48da1869db6e405b90ba54fdf50b8bc6

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08350014B2