Réaction #1605805

ord-2fa158d62ec74a38928f0596082c51e8

Équation de réaction

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
Rendement 171.2%

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.ADDITIONwere added
  2. 2
    Températurethe mixture was heated
  3. 3
    Autreremoved by a Dean-Stark trap
  4. 4
    ConcentrationThe reaction solution was concentrated under reduced pressure
  5. 5
    Autrea solid obtained
  6. 6
    Lavagewas washed with a mixed solvent of hexane-ethyl acetate (4:1)
  7. 7
    FiltrationThe solid was collected by filtration
  8. 8
    Autredried under reduced pressure

Mode opératoire

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).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09072734B2uspto-grants-2015_07