Reacción #960

ord-8f9821df03a7466091a3423b9a248655

Ecuación de reacción

CS(=O)(=O)OCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1
(3RS)-1-(N-benzyloxycarbonylamidino)-3-mesyloxymethyl pyrrolidine
[N-]=[N+]=[N-].[Na+]
sodium azide
O
Water
→
[N-]=[N+]=NCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1
product
Rendimiento 68.2%
[N-]=[N+]=NCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1
(3RS)-1-(N-benzyloxycarbonylamidino)-3-azidomethyl pyrrolidine
Rendimiento 68.2%

Reactantes

CS(=O)(=O)OCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1
(3RS)-1-(N-benzyloxycarbonylamidino)-3-mesyloxymethyl pyrrolidine
[N-]=[N+]=[N-].[Na+]
sodium azide
O
Water

Reactivos

Ninguno

Disolventes

CN(C)C=O
dimethylformamide

Condiciones de reacción

Temperatura
60°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Extracciónthe mixture was extracted twice with toluene/ethyl acetate 2/1
  2. 2
    SecadoThe combined organic layer was dried (Na2SO4)
  3. 3
    Filtraciónfiltered
  4. 4
    Otroevaporated
  5. 5
    OtroThe crude product was purified by flash chromatography

Procedimiento

0.450 g (1.27 mmole) (3RS)-1-(N-benzyloxycarbonylamidino)-3-mesyloxymethyl pyrrolidine and 0.124 g (1.9 mmole) of sodium azide were dissolved in 10 ml dimethylformamide and heated to 60° C. for four hours followed by stirring at room temperature over night. Water was added and the mixture was extracted twice with toluene/ethyl acetate 2/1. The combined organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified by flash chromatography using CH2Cl2 /MeOH 95/5 as eluent to yield 0.262 g (68%) of the product.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723444uspto-grants-1998_03