Реакция #1135834

ord-470e3ca4364144399d63742af1b622a4

Уравнение реакции

COC(=O)CCCCCCC(=O)Cl
methyl 8-chloro-8-oxooctanoate
Nc1cc(-c2ccccc2)ccc1[N+](=O)[O-]
4-nitrobiphenyl-3-amine
CCN(CC)CC
triethylamine
COC(=O)CCCCCCC(=O)Nc1cc(-c2ccccc2)ccc1[N+](=O)[O-]
methyl 8-(4-nitrobiphenyl-3-ylamino)-8-oxooctanoate
Выход 74.8%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Промывкаwashed with 1 N HCl, saturated sodium bicarbonate solution and brine
  2. 2
    КонцентрированиеThe separated organic layer was concentrated
  3. 3
    Другоеpurified by biotage column chromatography

Методика

To a solution of methyl 8-chloro-8-oxooctanoate (200 mg, 0.97 mmol) in DMF at 0° C. was added a solution of 4-nitrobiphenyl-3-amine (207 mg, 0.97 mmol) and triethylamine (0.46 mL, 3.3 mmol) in DMF drop-wise. The reaction was stirred overnight at room temperature, diluted with ethyl acetate and washed with 1 N HCl, saturated sodium bicarbonate solution and brine. The separated organic layer was concentrated and purified by biotage column chromatography to give methyl 8-(4-nitrobiphenyl-3-ylamino)-8-oxooctanoate (279 mg)

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09381196B2uspto-grants-2016_07