تفاعل #1890222

معادلة التفاعل

NaN3

Tf2O

TfN3

methyl 2-amino-3-(benzylsulfanyl)propanoate hydrochloride salt

→

azide

المردود 75.0%

Methyl 2-azido-3-(benzylsulfanyl)propanoate

المردود 75.0%

المذيبات

CH2Cl2

H2O

CH2Cl2

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe resulting solution was stirred for an additional 2 h
2. 2
   أخرىThe mixture was then placed in a separating funnel
3. 3
   أخرىthe organic layer was removed
4. 4
   استخلاصThe aqueous phase was extracted further with CH2Cl2 (2×3 mL)
5. 5
   غسيلwashed with saturated Na2CO3
6. 6
   تجفيفdried over Na2SO4(s)
7. 7
   ترشيحfiltered
8. 8
   تركيزThe mixture was concentrated under reduced pressure
9. 9
   أخرىpurified by silica gel flash chromatography
10. 10
    غسيلeluting with CH2Cl2

الإجراء التجريبي

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).

المصدر