Triethylamine → Ethyl 3-(1-ethyl-3-pyrrolecarboxamido)propionate

HRID 1737245Notes

Reaction equation

HRID 1737245 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=O)=[CH:4]1)[CH3:2].Cl.[CH2:12]([O:14][C:15](=[O:19])[CH2:16][CH2:17][NH2:18])[CH3:13].Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:3]1[CH:7]=[CH:6][C:5]([C:8]([NH:18][CH2:17][CH2:16][C:15]([O:14][CH2:12][CH3:13])=[O:19])=[O:10])=[CH:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 227379231-Ethyl-1H-pyrrole-3-carboxylic acid

Product 1

HCID 12146426Ethyl 3-(1-ethyl-3-pyrrolecarboxamido)propionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a suspension of 3.33 g (23.9 mmol) of 1-ethyl-3-pyrrolecarboxylic acid, 4.41 g (28.7 mmol) of β-alanine ethyl ester hydrochloride and 5.50 g (28.7 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride in 40 ml of methylene chloride, 4.0 ml (28.7 mmol) of triethylamine were added dropwise under ice cooling and stirring. The reaction mixture was stirred at room temperature for 2.5 hours.

Workup

  1. additionwere added dropwise under ice cooling
  2. stirringThe reaction mixture was stirred at room temperature for 2.5 hours

Sources & evidence

ORD record
ord-7e8c8fe2c8964d489b1d3482b1bb2a8f
Source dataset
uspto-grants-1999_10
Patent number
US05962448

Reaction notes

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