Tetrahydrofuran → (2-Cyano-5-{[cyano-(8-methoxy-4H-benzo[1,3]-dioxin-6-yl)methyl]amino}benzyl)carbamic Acid t-Butyl Ester

HRID 1157948노트

반응식

HRID 1157948 반응식
C1COCC1.[C:6]([O:10][C:11](=[O:23])[NH:12][CH2:13][C:14]1[CH:19]=[C:18]([NH2:20])[CH:17]=[CH:16][C:15]=1[C:21]#[N:22])([CH3:9])([CH3:8])[CH3:7].[CH3:24][O:25][C:26]1[C:35]2[O:34][CH2:33][O:32][CH2:31][C:30]=2[CH:29]=[C:28]([CH:36]=O)[CH:27]=1.C[Si]([C:42]#[N:43])(C)C>O.C(OCC)(=O)C>[C:6]([O:10][C:11](=[O:23])[NH:12][CH2:13][C:14]1[CH:19]=[C:18]([NH:20][CH:36]([C:42]#[N:43])[C:28]2[CH:27]=[C:26]([O:25][CH3:24])[C:35]3[O:34][CH2:33][O:32][CH2:31][C:30]=3[CH:29]=2)[CH:17]=[CH:16][C:15]=1[C:21]#[N:22])([CH3:9])([CH3:7])[CH3:8]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 82115Trimethylsilyl cyanideHCID 132668188-methoxy-4H-benzo[1,3]dioxine-6-carbaldehydeHCID 59511863(5-Amino-2-cyanobenzyl)carbamic acid t-butyl ester

생성물 1

HCID 25232250(2-Cyano-5-{[cyano-(8-methoxy-4H-benzo[1,3]-dioxin-6-yl)methyl]amino}benzyl)carbamic Acid t-Butyl Ester

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of Yb (OTf)3 (0.124 g) and THF (5 mL) there were added (5-amino-2-cyanobenzyl)carbamic acid t-butyl ester (Example (1g))(0.494 g), 8-methoxy-4H-benzo[1,3]dioxine-6-carboaldehyde (0.388 g), MS3A (0.5 g) and trimethylsilyl cyanide (0.533 mL) in that order under a nitrogen atmosphere, and the mixture was stirred at room temperature for 15 hours. Ethyl acetate (100 mL) and water (50 mL) were added to the mixture and filtration was performed with Celite. After sufficiently shaking the filtrate, the organic layer was separated off and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate, and the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture) to obtain the target compound (0.822 g) as a colorless solid.

후처리

  1. stirringAfter sufficiently shaking the filtrate
  2. customthe organic layer was separated off
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe mixture was filtered
  5. customto obtain a filtrate
  6. distillationthe solvent in the filtrate was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane mixture)

출처 및 근거

ORD 기록
ord-45415aa73e824259b7f68ecfaa4c432b
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07807690B2

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