반응 #1678439

반응 방정식

1-Methyl-2-chloromethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine

methyl-2(S)-amino-3-phenylpropionate

potassium carbonate

sodium iodide

→

1-methyl-2-[1-(S)-methoxycarbonyl-2-phenylethylamino]methyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine

용매

N,N-dimethylformamide

반응 조건

후처리

1. 1
   기타The solvent was then removed under reduced pressure
2. 2
   기타the residue was partitioned between ethyl acetate (100 ml) and saturated sodium bicarbonate solution (50 ml)
3. 3
   기타The phases were separated
4. 4
   세척the organic layer was washed with sodium bicarbonate solution and brine
5. 5
   건조dried (MgSO4)
6. 6
   농축concentrated
7. 7
   기타to yield 300 mg of crude product
8. 8
   기타The analytical product was obtained via chromatography on silica gel (ethyl acetate-hexane elution, 7:3 v/v) as a mixture of diasteriomers

실험 절차

1-Methyl-2-chloromethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine (150 mg, 0.5 mmole) and methyl-2(S)-amino-3-phenylpropionate (108 mg, 0.5 mmole) were combined in 4 ml of dry N,N-dimethylformamide, and potassium carbonate (138 mg, 1 mmole) and sodium iodide (70 mg, 0.5 mmole) were added to this mixture. The reaction mixture was protected from moisture and heated at 60° C. for 48 hours. The solvent was then removed under reduced pressure and the residue was partitioned between ethyl acetate (100 ml) and saturated sodium bicarbonate solution (50 ml). The phases were separated and the organic layer was washed with sodium bicarbonate solution and brine, then dried (MgSO4) and concentrated to yield 300 mg of crude product. The analytical product was obtained via chromatography on silica gel (ethyl acetate-hexane elution, 7:3 v/v) as a mixture of diasteriomers; 95% pure by HPLC.

출처