Réaction #969834

ord-851592ea8bfa43b4a6231cdd99e253c5

Équation de réaction

Cc1ccc(S(=O)(=O)O)cc1.NCCC(=O)OCc1ccccc1
4-methylbenzenesulphonic acid benzyl beta-alaninate
O=C(Cl)Oc1ccc([N+](=O)[O-])cc1
4-nitrophenyl chlorocarbonate
O=C(CCNC(=O)Oc1ccc([N+](=O)[O-])cc1)OCc1ccccc1
benzyl N-[(4-nitrophenoxy)carbonyl]-beta-alaninate

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurethe reaction mixture was then heated
  2. 2
    Températureto reflux for 30 min
  3. 3
    ConcentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  4. 4
    Autrethe residue was purified by means of preparative HPLC
  5. 5
    SéchageAfter concentration of the corresponding fractions and drying of the residue under high vacuum, 86 mg (44% of theory) of the title compound
  6. 6
    Autrewere obtained

Mode opératoire

200 mg (0.57 mmol) of commercially available 4-methylbenzenesulphonic acid-benzyl beta-alaninate and 229 mg (1.14 mmol) of 4-nitrophenyl chlorocarbonate were taken up in 15 ml of tetrahydrofuran and the reaction mixture was then heated to reflux for 30 min. Subsequently, the reaction mixture was concentrated under reduced pressure and the residue was purified by means of preparative HPLC. After concentration of the corresponding fractions and drying of the residue under high vacuum, 86 mg (44% of theory) of the title compound were obtained.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08992932B2uspto-grants-2015_03