Acetic Acid → HCID 68527178、化合物

HRID 884128ノート

反応式

HRID 884128 の反応式
[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

参加物

9

反応物 6

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 68524328HCID 68524328、化合物

生成物 1

HCID 68527178HCID 68527178、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aea7f5e10de0431f91ce0d0e16bf1a53
出典データセット
uspto-grants-2012_08
特許番号
US08236826B2

反応ノート

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