Sodium Hydroxide → HCID 69516187, 화합물

HRID 1297213노트

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HRID 1297213 반응식
[C:1]([N:20]1[N:24]=[N:23][C:22]([CH2:25][C:26]#[N:27])=[N:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C=O)CCCCC1.[OH-].[Na+].[I-].C[S+](C)(C)=O.[H-].[Na+].[CH:46]1([CH:52]=[C:53](C2N=NN(C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)N=2)C#N)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>C1C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.CCOC(C)=O>[CH:46]1([CH:52]2[CH2:53][C:25]2([C:22]2[N:23]=[N:24][N:20]([C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:21]=2)[C:26]#[N:27])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1

참가 물질

11

반응물 6

HCID 14798Sodium HydroxideHCID 16275CyclohexanecarboxaldehydeHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 58914637HCID 58914637, 화합물HCID 69516184HCID 69516184, 화합물

생성물 1

HCID 69516187HCID 69516187, 화합물수율 89.4%

시약·촉매·용매 4

HCID 74236Tetrabutylammonium Bromide촉매HCID 241Benzene용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (2-trityl-2H-tetrazol-5-yl)-acetonitrile (1.0 g, 2.85 mmol) in 15 mL benzene was added cyclohexanecarboxaldehyde (0.38 mL, 3.13 mmol), 10 mL 10% NaOH (aq), and tetrabutylammonium bromide (50 mg). The mixture was stirred for 1 h, then poured into EtOAc. The phases were separated, and the organic phase dried (MgSO4) and concentrated. Meanwhile, to trimethylsulfoxonium iodide (0.75 g, 3.42 mmol) in 7.0 mL DMF was added sodium hydride (60% dispersion in mineral oil, 0.14 g, 3.42 mmol). The mixture was stirred for 30 min at which time a solution of crude 3-cyclohexyl-2-(2-trityl-2H-tetrazol-5-yl)-acrylonitrile 2 (ca. 2.8 mmol) in 5.0 mL DMF was added quickly dropwise. The orange solution was stirred overnight, partitioned between EtOAc and H2O, and the phases separated. The organic phase was washed with brine, dried (MgSO4) and concentrated. Flash chromatography of the residue (15→20% EtOAc/hexanes) provided 1.15 g (88%, two steps) of 2-cyclohexyl-1-(2-trityl-2H-tetrazol-5-yl)-cyclopropanecarbonitrile as a colorless foam. 1H NMR (CDCl3) δ 7.33 (m, 9H), 7.07 (m, 6H), 1.88 (dd, J=4.9, 8.8 Hz, 1H, cyclopropyl —CHH), 1.66-1.84 (m, 4H), 1.57 (dd, J=4.9, 7.7 Hz, 1H, cyclopropyl —CHH), 1.25 (m, 8H).

후처리

  1. customThe phases were separated
  2. dry with materialthe organic phase dried (MgSO4)
  3. concentrationconcentrated
  4. additionwas added quickly dropwise
  5. stirringThe orange solution was stirred overnight
  6. custompartitioned between EtOAc and H2O
  7. customthe phases separated
  8. washThe organic phase was washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-f213cf0fa26f4df28c2bcb771a2f51ee
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250433B2

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