Water → 1-(1H-Imidazol-1-ylcarbonyl)-L-proline methyl ester

HRID 1425219Notes

Reaction equation

HRID 1425219 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][NH:6]1.C(N(CC)CC)C.[C:18](N1C=CN=C1)([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:19].O>ClCCl>[CH3:2][O:3][C:4](=[O:10])[C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[C:18]([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 675488891-(1H-Imidazol-1-ylcarbonyl)-L-proline methyl esterYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-proline methyl ester hydrochloride (0.300 g, 1.81 mmol) was dissolved in dichloromethane (5 ml). Triethylamine (0.202 g, 1.99 mmol) and 1,1′-carbonylbis-1H-imidazole (0.352 g, 2.17 mmol) were added, and the mixture was stirred at room temperature for five days. Water was added to the reaction solution, followed by extraction with dichloromethane. Then, the organic layer was washed with brine and dried over anhydrous sodium sulfate. Following concentration under reduced pressure, 0.404 g of the title compound was obtained as a colorless oily substance (100%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThen, the organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentration under reduced pressure

Sources & evidence

ORD record
ord-07721259974b4479a3d30cde53b4a3cb
Source dataset
uspto-grants-2015_01
Patent number
US08927588B2

Reaction notes

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