Ethyl Acetate → 6-(Di-pyridin-2-yl-amino)-hexanoic acid methyl ester

HRID 404134

반응식

HRID 404134 반응식
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23].CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[CH3:25][O:24][C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][N:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][N:3]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 145472,2'-DipyridylamineHCID 24758Sodium hydrideHCID 4170292Methyl 6-Bromohexanoate

생성물 1

HCID 585450216-(Di-pyridin-2-yl-amino)-hexanoic acid methyl ester수율 24%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
90 °C

실험 절차

NaH (112 mg, 2.92 mmol) was added to di-pyridin-2-yl-amine (500 mg, 2.92 mmol) in DMF (10 mL) at rt. After 10 min, KI (485 mg, 2.92 mmol) and methyl 6-bromohexanoate, I (0.464 mL, 2.92 mmol) were added, and the reaction mixture was stirred at 90° C. for 21 h. Brine (200 mL) and EtOAc (200 mL) were then added, the phases were separated, and the aqueous phase was extracted with EtOAc (100 mL). The organic phases were combined, dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using CH2Cl2/MeOH (100:0.5 to 100:1) as eluant to furnish II as a colourless oil (206 mg, 24%).

후처리

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customsubsequently evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-9a11980996a44e3fa56ecda51bb47bfd
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748458B2

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