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

HRID 256547

Reaction equation

HRID 256547 reaction equation
[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

Participants

4

Reactant 2

HCID 795ImidazoleHCID 10912012Benzyl 2-Benzylacrylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-31d51074cc414e9388d23cc517fb544b
Source dataset
uspto-grants-1993_11
Patent number
US05258362

Linked notes

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