Imidazole → Benzyl (2RS)-2-Benzyl-3-(imidazol-1-yl)propionate

HRID 256547

반응식

HRID 256547 반응식
[CH2:1]([C:8](=[CH2:19])[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:20]1[CH:24]=[CH:23][N:22]=[CH:21]1>C(#N)C>[CH2:1]([CH:8]([CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)[C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 795ImidazoleHCID 10912012Benzyl 2-Benzylacrylate

생성물 1

HCID 54041659Benzyl (2RS)-2-Benzyl-3-(imidazol-1-yl)propionate수율 94.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

The resultant compound from Example 73 (10.00 g, 36.93 mmol) and imidazole (5.40 g, 79.3 mmol) in acetonitrile (10 mL) were heated at reflux for 44 h. The mixture was evaporated and the residue was chromatographed on silica gel with 2% methanol in chloroform to afford 11.20 g (88%) of the desired product as an oil: TLC (5% methanol/95% chloroform) Rf =0.35; 1H-NMR (CDCl3) 7.38 (s, 1H), 7.38-7.05 (m, 10H), 7.00 (dd, 1H), 6.80 (dd, 1H), 5.03 (d, 1H), 4.99 (d, 1H), 4.25 (1H), 4.03 (dd, 1H), 3.22-3.09 (m, 1H), 3.02 (dd, 1H), 2.78 (dd, 1H).

후처리

  1. temperatureat reflux for 44 h
  2. customThe mixture was evaporated
  3. customthe residue was chromatographed on silica gel with 2% methanol in chloroform

출처 및 근거

ORD 기록
ord-31d51074cc414e9388d23cc517fb544b
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258362

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