반응 #969847

반응 방정식

Methyl 4-bromo-2-sulfo-butyrate

sodium azide

→

title compound

수율 95.0%

Methyl 4-azido-2-sulfo-butyrate

수율 95.0%

용매

DMF

반응 조건

후처리

1. 1
   기타The mixture was evaporated
2. 2
   기타purified by SiO2 chromatography
3. 3
   세척eluted with CH3OH/CH2Cl2/HAc
4. 4
   기타crystallized with CH3OH/Toluene/Hexane

실험 절차

Methyl 4-bromo-2-sulfo-butyrate (1.07 g, 4.11 mmol) and sodium azide (0.70 g (10.7 mmol) in DMF (50 ml) was stirred overnight. The mixture was evaporated and purified by SiO2 chromatography and eluted with CH3OH/CH2Cl2/HAc and crystallized with CH3OH/Toluene/Hexane to afford 1.00 g (95%) of the title compound. m.p=267-272° C. (decomp). 1H NMR (DMF-d7): 12.06 (br, 1H), 3.65 (s, 3H), 3.59 (dd, 1H, J=5.4, 8.9 Hz), 3.47 (m, 2H), 2.24 (m, 2H). 13C NMR 171.10, 64.29, 52.24, 50.64, 21.35. ESI MS m/z+267.9 (M+2Na−H), m/z−222.0 (M−H). HRMS m/z−(C5H9N3O5S−H) calcd 222.0185, found 222.0179.

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