Reaktion #42319

ord-3e4998293c48493baeca79bddc9ed4da

Reaktionsgleichung

O=C(O)CCCOCc1ccccc1
4-benzyloxybutyric acid
CCCN
propylamine
On1nnc2ccccc21
HOBt
CN1CCOCC1
N-methylmorpholine
ClCCCl
EDC
CCCNC(=O)CCCOCc1ccccc1
4-(benzyloxy)-N-propylbutanamide
Ausbeute 79.8%

Lösungsmittel

Reaktionsbedingungen

Temperatur
22.5°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with water (10 mL), hydrochloric acid (1 N, 10 mL), saturated sodium bicarbonate (10 mL), and saline (10 mL)
  2. 2
    SonstigeThe organic phase is separated
  3. 3
    Trocknendried over magnesium sulfate
  4. 4
    Filtrationfiltered
  5. 5
    Einengenconcentrated under reduced pressure

Vorschrift

A mixture of 4-benzyloxybutyric acid (2.69 g, 13.8 mmol), propylamine (0.82 g, 13.8 mmol), HOBt (2.05 g, 15.2 mmol), N-methylmorpholine (1.68 g, 16.6 mmol) and EDC (2.91 g, 15.2 mmol) in DMF (6 mL) is stirred at 20-25 degrees C. for 18 hours. The mixture is diluted with ethyl acetate (40 mL) and washed with water (10 mL), hydrochloric acid (1 N, 10 mL), saturated sodium bicarbonate (10 mL), and saline (10 mL). The organic phase is separated, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to provide 4-(benzyloxy)-N-propylbutanamide (2.59 g), APCI-MS (m/z) [M+H]+=236.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07727997B2uspto-grants-2010_06