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

HRID 43745

Reaction equation

HRID 43745 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, 0.404g 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-86d9760c76fb49ea90d9def8ad4650fb
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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