Reacción #969847

ord-db050d71897a44cd93d2f28ece6cd30f

Ecuación de reacción

COC(=O)C(CCBr)S(=O)(=O)O
Methyl 4-bromo-2-sulfo-butyrate
[N-]=[N+]=[N-].[Na+]
sodium azide
→
COC(=O)C(CCN=[N+]=[N-])S(=O)(=O)O
title compound
Rendimiento 95.0%
COC(=O)C(CCN=[N+]=[N-])S(=O)(=O)O
Methyl 4-azido-2-sulfo-butyrate
Rendimiento 95.0%

Reactantes

COC(=O)C(CCBr)S(=O)(=O)O
Methyl 4-bromo-2-sulfo-butyrate
[N-]=[N+]=[N-].[Na+]
sodium azide

Reactivos

Ninguno

Disolventes

CN(C)C=O
DMF

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe mixture was evaporated
  2. 2
    Otropurified by SiO2 chromatography
  3. 3
    Lavadoeluted with CH3OH/CH2Cl2/HAc
  4. 4
    Otrocrystallized with CH3OH/Toluene/Hexane

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08236319B2uspto-grants-2012_08