Реакция #960

ord-8f9821df03a7466091a3423b9a248655

Уравнение реакции

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
Выход 68.2%
[N-]=[N+]=NCC1CCN(C(=N)NC(=O)OCc2ccccc2)C1
(3RS)-1-(N-benzyloxycarbonylamidino)-3-azidomethyl pyrrolidine
Выход 68.2%

Реактанты

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

Реагенты

Нет

Растворители

CN(C)C=O
dimethylformamide

Условия реакции

Температура
60°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Экстракцияthe mixture was extracted twice with toluene/ethyl acetate 2/1
  2. 2
    СушкаThe combined organic layer was dried (Na2SO4)
  3. 3
    Фильтрацияfiltered
  4. 4
    Другоеevaporated
  5. 5
    ДругоеThe crude product was purified by flash chromatography

Методика

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.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US05723444uspto-grants-1998_03