Reaktion #51181

Reaktionsgleichung

1-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride

1-hydroxy-7-azabenzotriazole

methyl 3-amino-3-(3-fluorophenyl)propanoate hydrochloride

N,N-diisopropylethylamine

5-oxo-1-(3-{(benzylamino)carbonylamino}phenyl)pyrrolidine-3-carboxylic acid

→

title compound

Methyl 3-(3-fluorophenyl)-3-{(5-oxo-1-(3-{(benzylamino)carbonylamino}phenyl)pyrrolidin-3-yl)carbonylamino}propanoate

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction was partitioned between an aqueous solution of hydrochloric acid (1.5 N, 20 mL) and ethyl acetate (3×25 mL)
2. 2
   TrocknenThe combined organic layers were dried over sodium sulfate
3. 3
   Filtrationwere filtered
4. 4
   Einengenwere concentrated in vacuo
5. 5
   SonstigeThe residue was purified by flash column chromatography (90% ethyl acetate in hexanes)

Vorschrift

1-(3-(Dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride (99.5 mg, 0.52 mmol, 1.2 equiv), 1-hydroxy-7-azabenzotriazole (12.2 mg, 0.090 mmol, 0.2 equiv), methyl 3-amino-3-(3-fluorophenyl)propanoate hydrochloride (118.8 mg, 0.51 mmol, 1.2 equiv), and N,N-diisopropylethylamine (0.18 mL, 1.03 mmol, 2.4 equiv) were added sequentially to a solution of 5-oxo-1-(3-{(benzylamino)carbonylamino}phenyl)pyrrolidine-3-carboxylic acid (152.2 mg, 0.43 mmol, 1 equiv) in N,N-dimethylformamide (3.0 mL). The resulting solution was stirred at 23° C. for 92 hr. The reaction was partitioned between an aqueous solution of hydrochloric acid (1.5 N, 20 mL) and ethyl acetate (3×25 mL). The combined organic layers were dried over sodium sulfate, were filtered, and were concentrated in vacuo. The residue was purified by flash column chromatography (90% ethyl acetate in hexanes) to give two diastereomers of the title compound (first diastereomer and second diastereomer) as white solids.

Quelle