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tert-Butyl {1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate → tert-Butyl{1-[2-(6-chloro-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate

HRID 1644505
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HRID 1644505 반응식
[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=3[N+:19]([O-])=[N:18][C:17]2=[O:28])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.O.[Zn]>[C:1]([O:5][C:6](=[O:29])[NH:7][CH:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([Cl:26])[CH:24]=[CH:25][C:20]=3[N:19]=[N:18][C:17]2=[O:28])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 1

HCID 86642661tert-Butyl {1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate2회

생성물 1

HCID 86664539tert-Butyl{1-[2-(6-chloro-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate수율 16%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 176Acetic Acid용매HCID 962Water
용매

실험 절차

To a solution of tert-butyl{1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 206) (0.43 g) in acetic acid (8 mL) and water (2 mL) was added zinc dust (0.50 g). After 30 minutes, the solution was filtered and the filtrate concentrated. The residue was then treated with potassium ferricyanide (1.0 g) in water (20 mL). After 2 hours, the reaction was diluted with ethyl acetate. The aqueous layer was collected, the pH adjusted with solid Na2CO3 and extracted with ethyl acetate. The combined organic washes were dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography on silica gel with 0-25% acetone in dichloromethane to yield 66 mg of the product.

후처리

  1. filtrationthe solution was filtered
  2. concentrationthe filtrate concentrated
  3. additionThe residue was then treated with potassium ferricyanide (1.0 g) in water (20 mL)
  4. waitAfter 2 hours
  5. additionthe reaction was diluted with ethyl acetate
  6. customThe aqueous layer was collected
  7. extractionextracted with ethyl acetate
  8. dry with materialThe combined organic washes were dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified by chromatography on silica gel with 0-25% acetone in dichloromethane

출처 및 근거

ORD 기록
ord-b1640e8af56d429db2290c3d1c2db38c
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08124602B2

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