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

HRID 1384082Notes

Reaction equation

HRID 1384082 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-f403f7af6b2f402fbc895f5220eeaa4a
Source dataset
uspto-grants-2001_07
Patent number
US06258805B1

Reaction notes

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