Реакция #1726714

ord-91672ebaa4c447ba80fc0de360d6ee39

Уравнение реакции

[NH4+].[OH-]
ammonium hydroxide
COC(=O)c1ccc(OCc2ccccc2)c(C(=O)O)c1
methyl 4-benzyloxy-3-carboxybenzoate
On1nnc2ccccc21
HOBT
CCN=C=NCCCN(C)C
1-ethyl-3-(3-dimethylaminopropyl)carbodiimide
COC(=O)c1ccc(OCc2ccccc2)c(C(N)=O)c1
methyl 4-benzyloxy-3-carbamoylbenzoate
Выход 92.3%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    КонцентрированиеThe reaction mixture is concentrated
  2. 2
    Другоеto remove most of the DMF
  3. 3
    ПромывкаThe ethyl acetate solution is washed with brine
  4. 4
    Сушкаdried over Na2SO4
  5. 5
    ДругоеRemoval of solvent by rotoevaporation

Методика

To a solution of 1.5 gm (5.2 mmol) of methyl 4-benzyloxy-3-carboxybenzoate in 8 mL of DMF is added 0.85 gm (6.2 mmol) of HOBT and 1.2 gm (6.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC). After 1 hr, 0.86 mL of 30% ammonium hydroxide is added, and the solution stirred for an additional 2 hr. The reaction mixture is concentrated to remove most of the DMF, and the residue is taken up in ethyl acetate. The ethyl acetate solution is washed with brine and dried over Na2SO4. Removal of solvent by rotoevaporation gives 1.37 gm (4.8 mmol) of methyl 4-benzyloxy-3-carbamoylbenzoate.

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08110570B2uspto-grants-2012_02