4-(4-Chlorophenyl)-3-(3-cyanophenyl)-2-azidobutane → 3-((2S,3S)-3-amino-1-(4-chlorophenyl)butan-2-yl)benzonitrile

HRID 2354503

반응식

HRID 2354503 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)[CH:10]([N:12]=[N+]=[N-])[CH3:11])=[CH:4][CH:3]=1>C(OC(C)C)(=O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)[C@@H:10]([NH2:12])[CH3:11])=[CH:4][CH:3]=1

참가 물질

4

반응물 1

HCID 116811424-(4-Chlorophenyl)-3-(3-cyanophenyl)-2-azidobutane

생성물 1

HCID 115872963-((2S,3S)-3-amino-1-(4-chlorophenyl)butan-2-yl)benzonitrile

시약·촉매·용매 2

HCID 131709914Lindlars catalyst촉매HCID 7915Isopropyl Acetate용매

반응 조건

온도
21.5 °C

실험 절차

To a solution of 4-(4-chlorophenyl)-3-(3-cyanophenyl)-2-azidobutane (650 g, 2.1 mol) in isopropyl acetate (3.3 L) was added Lindlar's catalyst (130 g), and the mixture was hydrogenated at 40 psi at 45° C. for 24 h and at room temperature for anther 48 h. The reaction mixture was filtered over solka floc, and the cake was washed thoroughly with isopropyl acetate. The filtrate was partially concentrated to approximately 6 L, and was added hydrogen chloride in isopropyl acetate (5-6 N) while maintaining the reaction temperature at 18-25° C. After aging overnight, the precipitate was collected by filtration and washed twice with isopropyl acetate (1 L×2). The precipitate was suspended in isopropyl acetate (5.8 L) and was added aqueous potassium carbonate (1 M, 3.5 L). After stirring for 20 min, the organic layer was separated and concentrated to an oil, which was purified by preparative HPLC eluting on a Chiralpak AD column with heptane/ethanol/diethylamine (70/30/0.1; flow rate: 700 mL/min) to give the title compound.

후처리

  1. filtrationThe reaction mixture was filtered over solka floc
  2. washthe cake was washed thoroughly with isopropyl acetate
  3. concentrationThe filtrate was partially concentrated to approximately 6 L
  4. additionwas added hydrogen chloride in isopropyl acetate (5-6 N)
  5. waitAfter aging overnight
  6. filtrationthe precipitate was collected by filtration
  7. washwashed twice with isopropyl acetate (1 L×2)
  8. additionwas added aqueous potassium carbonate (1 M, 3.5 L)
  9. customthe organic layer was separated
  10. concentrationconcentrated to an oil, which
  11. customwas purified by preparative HPLC
  12. washeluting on a Chiralpak AD column with heptane/ethanol/diethylamine (70/30/0.1; flow rate: 700 mL/min)

출처 및 근거

ORD 기록
ord-f74c6c3e2e154a0c9708b8ad429ef3a3
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07754188B2

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