Реакция #1697984

ord-a73614eb32cd4e089303c1e43a2034d0

Уравнение реакции

CS(=O)(=O)OCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1
1-benzyloxycarbonylamidino-4-mesyloxyethyl piperidine
[N-]=[N+]=[N-].[Na+]
sodium azide
O
water
→
[N-]=[N+]=NCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1
4-Azidoethyl-1-benzyloxycarbonylamidino piperidine

Реактанты

CS(=O)(=O)OCCC1CCN(C(=N)NC(=O)OCc2ccccc2)CC1
1-benzyloxycarbonylamidino-4-mesyloxyethyl piperidine
[N-]=[N+]=[N-].[Na+]
sodium azide
O
water

Реагенты

Нет

Растворители

CN(C)C=O
dimethylformamide

Условия реакции

Температура
100°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    workup.ADDITIONwas added
  2. 2
    Экстракцияextracted with ethyl acetate three times
  3. 3
    ПромывкаThe combined organic phase was washed with water
  4. 4
    Сушкаdried (Na2SO4)
  5. 5
    Другоеevaporated
  6. 6
    Другоеchromatographed on silica gel

Методика

In 100 ml of dimethylformamide was dissolved 4.4 g (0.0115 mol) of crude 1-benzyloxycarbonylamidino-4-mesyloxyethyl piperidine and 4.5 g (0.069 Mol) of sodium azide was added. The mixture was heated at 100° C. for 2.5 h. It was then poured into water and extracted with ethyl acetate three times. The combined organic phase was washed with water, dried (Na2SO4) and evaporated. The residue was flash chromatographed on silica gel using ethyl acetate/heptane 1/1 as eluent. Yield: 3.0 g (79%).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US06984627B1uspto-grants-2006_01