Reacción #1483077

ord-7d57691e8f6b4d8ca9c8631a0e278a01

Ecuación de reacción

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
Rendimiento 98.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Concentraciónconcentrated in vacuo
  2. 2
    workup.ADDITIONThe remaining residue was diluted with ethyl acetate (20 mL)
  3. 3
    Lavadowashed with 1N HCl (20 mL)
  4. 4
    SecadoThe organic layer was dried over MgSO4
  5. 5
    Filtraciónfiltered
  6. 6
    Concentraciónconcentrated

Procedimiento

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).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08900565B2uspto-grants-2014_12