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

HRID 256547

反応式

HRID 256547 の反応式
[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

参加物

4

反応物 2

HCID 795ImidazoleHCID 10912012Benzyl 2-Benzylacrylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-31d51074cc414e9388d23cc517fb544b
出典データセット
uspto-grants-1993_11
特許番号
US05258362

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