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

HRID 2296903Notes

Reaction equation

HRID 2296903 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-1518214905394e788170e34add59507a
Source dataset
uspto-grants-2002_12
Patent number
US06489473B2

Reaction notes

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