Реакция #1483077

ord-7d57691e8f6b4d8ca9c8631a0e278a01

Уравнение реакции

COC(=O)c1ccc2c(c1)c(Cc1ccc(NC(=O)c3ccccc3)cc1)cn2C
3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester
[Na+].[OH-]
sodium hydroxide
CO
methanol
O
water
Cn1cc(Cc2ccc(NC(=O)c3ccccc3)cc2)c2cc(C(=O)O)ccc21
3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid
Выход 98.0%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    Концентрированиеconcentrated in vacuo
  2. 2
    workup.ADDITIONThe remaining residue was diluted with ethyl acetate (20 mL)
  3. 3
    Промывкаwashed with 1N HCl (20 mL)
  4. 4
    СушкаThe organic layer was dried over MgSO4
  5. 5
    Фильтрацияfiltered
  6. 6
    Концентрированиеconcentrated

Методика

A solution of 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid methyl ester (69 mg, 0.17 mmol), sodium hydroxide (21 mg, 0.52 mmol), methanol (3 mL), water (1 mL) and THF (3 mL) was heated to 60° C. for 24 hr. The reaction solution was then cooled to room temperature and concentrated in vacuo. The remaining residue was diluted with ethyl acetate (20 mL) and washed with 1N HCl (20 mL). The organic layer was dried over MgSO4, filtered and concentrated to provide 3-(4-benzoylamino-phenylmethyl)-1-methyl-1H-indole-5-carboxylic acid (64 mg, 98% yield).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US08900565B2uspto-grants-2014_12