Ethyl benzoylacetate → HCID 10923588, 화합물

HRID 724828노트

반응식

HRID 724828 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 10923588HCID 10923588, 화합물수율 62%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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%)

출처 및 근거

ORD 기록
ord-9ec9191673d841cb80b2ff1164cfb320
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705504

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