Reaktion #92203

Reaktionsgleichung

ethyl 2-amino-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylate

benzoyl isocyanate

→

ethyl 2-(3-benzoylureido)-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylate

Ausbeute 22.3%

Lösungsmittel

toluene

water

EA

Reaktionsbedingungen

Aufarbeitung

1. 1
   TrocknenThe organic layer was dried over Na2SO4
2. 2
   Einengenconcentrated to a residue which
3. 3
   Sonstigewas purified by Prep HPLC

Vorschrift

To a solution of ethyl 2-amino-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylate (38.9 mg, 0.1 mmol) in toluene (5 mL) was added benzoyl isocyanate (14.7 mg, 0.1 mmol). The reaction was stirred at RT for 2 h then diluted with EA (5 mL) and water (2 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give ethyl 2-(3-benzoylureido)-4-(4-chlorobenzyl)-5-(3-chlorophenyl)furan-3-carboxylate (12 mg, 22% yield) as a white solid. 1H NMR (DMSO-d6) δ: 12.41 (s, 1H), 11.51 (s, 1H), 8.10 (d, J=7.4 Hz, 2H), 7.75 (t, J=7.5 Hz, 1H), 7.63 (t, J=7.7 Hz, 2H), 7.60-7.51 (m, 3H), 7.48 (d, J=6.9 Hz, 1H), 7.42 (d, J=8.5 Hz, 2H), 7.27 (d, J=8.3 Hz, 2H), 4.34 (s, 2H), 4.28 (q, J=7.1 Hz, 2H), 1.23 (t, J=7.1 Hz, 3H). LCMS: MH+ 537 and TR=2.962 min.

Quelle