Acetic Acid → HCID 68527178, 화합물

HRID 884128노트

반응식

HRID 884128 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]=[CH:28][C:29]=1[Cl:30])[CH2:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([CH2:20]CC(OCC)=O)=[CH:16][CH:15]=2)=[N:11][CH:12]=1.C=O.[C:33]([OH:36])(=[O:35])[CH3:34].[C:37]([BH3-])#N.[Na+].[OH-].[Na+].Cl>C(O)C.O>[Cl:30][C:29]1[CH:28]=[C:27]([CH:37]=[CH:3][C:2]=1[Cl:1])[CH2:4][CH2:5][NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][C:14]2[CH:15]=[CH:16][C:17]([CH2:20][CH2:34][C:33]([OH:36])=[O:35])=[CH:18][CH:19]=2)=[N:11][CH:12]=1

참가 물질

9

반응물 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 68524328HCID 68524328, 화합물

생성물 1

HCID 68527178HCID 68527178, 화합물

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

To a solution of ethyl 3-{4-[5-(3,4-dichlorobenzylamino)pyridin-2-yloxy]phenyl}propionate (1.63 g, 3.7 mmol) in ethanol (30 mL) were added 37% aqueous formaldehyde (2.0 mL, 22 mmol) and acetic acid (0.21 mL, 3.7 mmol), and the resulting solution was stirred at room temperature for 1 hour. To this solution was then added sodium cyanoborohydride (0.46 g, 7.3 mmol) at 0° C., and the resulting solution was stirred at the same temperature for 1 hour. To this solution was added water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1), to thereby yield 1.55 g of ethyl 3-{4-[5-(3,4-dichlorobenzylmethylamino)-pyridin-2-yloxy]phenyl}propionate. This product was dissolved in ethanol (40 mL), and to the resulting solution was added 10% aqueous sodium hydroxide (2.7 mL, 6.7 mmol) and stirred at room temperature for 2 hours. The resulting solution was then acidified by adding 10% hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried over anhydrous magnesium sulfate, and evaporated, to thereby yield 1.44 g of the title compound.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)
  6. dissolutionThis product was dissolved in ethanol (40 mL)
  7. stirringstirred at room temperature for 2 hours
  8. extractionextracted with ethyl acetate
  9. washThe ethyl acetate layer was washed with water
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customevaporated

출처 및 근거

ORD 기록
ord-aea7f5e10de0431f91ce0d0e16bf1a53
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08236826B2

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