Sodium Iodide → HCID 18611564, 화합물

HRID 1591257

반응식

HRID 1591257 반응식
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:5][CH2:4][CH:3]1[CH2:20]Cl.[CH3:22][O:23][C:24](=[O:34])[C@@H:25]([NH2:33])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O>[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])=[N:5][CH2:4][CH:3]1[CH2:20][NH:33][C@H:25]([C:24]([O:23][CH3:22])=[O:34])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 736234L-Phenylalanine, methyl esterHCID 134856441-methyl-2-chloromethyl-5-(2'-fluorophenyl)-2,3-dihydro-1H-1,4-benzodiazepine

생성물 1

HCID 18611564HCID 18611564, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

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.

후처리

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

출처 및 근거

ORD 기록
ord-699fa4b18c464ab78805eac6dab83587
출처 데이터셋
uspto-grants-1993_04
특허 번호
US05206238

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