Triethylamine → ethyl N-methyl-3-(3-pyrrolecarboxamido)propionate

HRID 322611Notes

Reaction equation

HRID 322611 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.[CH3:9][NH:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH3:9][N:10]([CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:6]([C:3]1[CH:4]=[CH:5][NH:1][CH:2]=1)=[O:8]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 101030Pyrrole-3-carboxylic acidHCID 541480Ethyl 3-(methylamino)propanoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 53878575ethyl N-methyl-3-(3-pyrrolecarboxamido)propionateYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Procedure

Into a suspension of 3.30 g (30 mmol) of 3-pyrrolecarboxylic acid in 10 me of dichloromethane, a solution of 5.90 g (45 mmol) of ethyl N-methyl-3-aminopropionate in 50 ml of dichloromethane, a solution of 4.55 g (45 mmol) of triethylamine in 50 ml of dichloromethane, and 8.63 g (45 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride were successively added, followed by stirring at room temperature for 3 hours. Dichloromethane was added to the reaction mixture, and the resulting organic layer was washed successively with a 10% aqueous solution of citric acid, a saturated aqueous solution of sodium hydrogencarbonate and a saturated aqueous solution of sodium chloride. The organic layer was dried over anhydrous magnesium sulfate and was then concentrated under reduced pressure, whereby 5.31 g of the title compound were obtained (yield: 79%).

Workup

  1. washthe resulting organic layer was washed successively with a 10% aqueous solution of citric acid
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationwas then concentrated under reduced pressure

Sources & evidence

ORD record
ord-fe34bd222d87491697457e93e13595c7
Source dataset
uspto-grants-2001_04
Patent number
US06211362B1

Reaction notes

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