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

HRID 51234

Reaction equation

HRID 51234 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-bcbd69472e4d41af916ac052054b1c80
Source dataset
uspto-grants-2004_03
Patent number
US06713634B2

Linked notes

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