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Sodium Bicarbonate → tert-butyl (2-oxo-2-(pyridin-2-ylamino)ethyl)(1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate

HRID 2193158
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HRID 2193158 반응식
[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:14][C:15](=[O:23])[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[O:25]=[C:26]1[CH:35]=[N:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]1[CH2:36][CH:37]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.ClCCl>[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:14][C:15](=[O:23])[NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1)[CH:8]1[CH2:9][CH2:10][N:11]([CH2:37][CH2:36][N:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:34]=[CH:35][C:26]2=[O:25])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]
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참가 물질

8

반응물 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59397888(2-oxoquinoxalin-1(2H)-yl)acetaldehydeHCID 59398033HCID 59398033, 화합물

생성물 1

HCID 59398373tert-butyl (2-oxo-2-(pyridin-2-ylamino)ethyl)(1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate수율 96.6%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6212Chloroform용매HCID 6344Dichloromethane용매

실험 절차

To 3 mL of dichloromethane solution containing 0.18 g of tert-butyl(2-oxo-2-(pyridin-2-ylamino)ethyl)(piperidin-4-yl)carbamate, 0.10 g of (2-oxoquinoxalin-1(2H)-yl)acetaldehyde and 30 μl of acetic acid were added and stirred at room temperature for 2 hours. To the reaction mixture, 0.17 g of sodium triacetoxyborohydride was added and stirred at the same temperature for 30 min. Chloroform and aqueous saturated sodium hydrogen carbonate solution were added, the organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and extracts were combined, washed sequentially with water and aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=10:1] to give 0.26 g of tert-butyl(2-oxo-2-(pyridin-2-ylamino)ethyl)(1-(2-(2-oxoquinoxalin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate as a pale yellow foam.

후처리

  1. additionwere added
  2. stirringstirred at the same temperature for 30 min
  3. customthe organic layer was separated
  4. extractionthe aqueous layer was extracted with chloroform
  5. washwashed sequentially with water and aqueous saturated sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=10:1]

출처 및 근거

ORD 기록
ord-fde927945ba2402eab3654e1d44108f3
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08329694B2

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