Triethylamine → HCID 53772128, compound

HRID 1590805Notes

Reaction equation

HRID 1590805 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:17])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Cl.[CH3:20][O:21][C:22](=[O:28])[C@@H:23]1[CH2:27][CH2:26][CH2:25][NH:24]1>C(Cl)Cl>[CH3:20][O:21][C:22](=[O:28])[C@@H:23]1[CH2:27][CH2:26][CH2:25][N:24]1[C:8](=[O:17])[CH:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660233-Phenylprop-2-enoyl chlorideHCID 2733200methyl L-prolinate hydrochloride

Product 1

HCID 53772128HCID 53772128, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (25.26 ml) and cinnamoyl chloride (16.60 g) were successively added to a methylene chloride solution (300 ml) of L-proline methylester hydrochloride (15.0 g) under ice cooling, and the mixture was stirred under ice cooling for 30 minutes. After stirring at room temperature for 1.5 hours, the mixture was poured into ice water and successively washed with 1N hydrochloric acid, saturated sodium hydrogencarbonate, and saturated salt water, dried over magnesium sulfate, and concentrated. The residue was purified by silica gel column chromatography to obtain 23.09 g of N-cinnamoyl-L-proline methyl ester.

Workup

  1. stirringAfter stirring at room temperature for 1.5 hours
  2. washsuccessively washed with 1N hydrochloric acid, saturated sodium hydrogencarbonate, and saturated salt water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-13af48565e5e437c9364f6f7ed0e97f7
Source dataset
uspto-grants-1993_04
Patent number
US05204462

Reaction notes

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