Reacción #1605805

ord-2fa158d62ec74a38928f0596082c51e8

Ecuación de reacción

Nc1cc(CCCC(=O)O)ccc1-c1ccccc1
4-(3-Amino-4-phenylphenyl)butyric acid
Cc1ccc(S(=O)(=O)O)cc1.O
tosylic acid hydrate
O
water
Cc1ccc(S(=O)(=O)O)cc1.Nc1cc(CCCC(=O)OCc2ccccc2)ccc1-c1ccccc1
benzyl 4-(3-amino-4-phenylphenyl)butyrate tosylate
Rendimiento 171.2%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwere added
  2. 2
    Temperaturathe mixture was heated
  3. 3
    Otroremoved by a Dean-Stark trap
  4. 4
    ConcentraciónThe reaction solution was concentrated under reduced pressure
  5. 5
    Otroa solid obtained
  6. 6
    Lavadowas washed with a mixed solvent of hexane-ethyl acetate (4:1)
  7. 7
    FiltraciónThe solid was collected by filtration
  8. 8
    Otrodried under reduced pressure

Procedimiento

To a suspension of 4-(3-Amino-4-phenylphenyl)butyric acid (21.6 g, 84.6 mmol) in toluene (300 mL), benzyl alcohol (50 mL) and tosylic acid hydrate (17.7 g, 93.0 mmol) were added, and the mixture was heated under reflux for 5 hours with water removed by a Dean-Stark trap. The reaction solution was concentrated under reduced pressure and a solid obtained was washed with a mixed solvent of hexane-ethyl acetate (4:1). The solid was collected by filtration and dried under reduced pressure to obtain benzyl 4-(3-amino-4-phenylphenyl)butyrate tosylate (41.2 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09072734B2uspto-grants-2015_07