Ethyl benzoylacetate → HCID 10923588、化合物

HRID 724828ノート

反応式

HRID 724828 の反応式
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:9]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[BH3-]C#N.[Na+]>CO>[C:10]1([CH:9]([NH:2][C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 7170Ethyl benzoylacetateHCID 8870Benzenamine hydrochloride (1:1)HCID 5003444Sodium cyanoborohydride

生成物 1

HCID 10923588HCID 10923588、化合物収率 62%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of aniline hydrochloride (3.37 g, 26 mmol) and ethyl benzoylacetate (5 mL, 26 mmol) in MeOH (70 mL) was added NaBH3CN (1.75 g) and the mixture was stirred at room temperature for 18 h. The solvent was removed and the residue partitioned between 0.5N HCl and Et20. The aqueous phase was made basic with 1N NaOH and extracted with CHCl3. The organic phase was dried and concentrated to a residue. Purification by chromatography on silica gel (hexane: EtOAc, 5%) afforded ethyl 3-phenyl-3-(phenylamino)propionate (4.3 g, 62%). This compound was then hydrolized under basic conditions to give the title compound as a white solid.

後処理

  1. customThe solvent was removed
  2. customthe residue partitioned between 0.5N HCl and Et20
  3. extractionextracted with CHCl3
  4. customThe organic phase was dried
  5. concentrationconcentrated to a residue
  6. customPurification by chromatography on silica gel (hexane: EtOAc, 5%)

出典と根拠

ORDレコード
ord-9ec9191673d841cb80b2ff1164cfb320
出典データセット
uspto-grants-1998_01
特許番号
US05705504

反応ノート

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