Triethylamine → Ethyl 3-(4-methyl-3-pyrrolecarboxamido)propionate

HRID 51235

Reaction equation

HRID 51235 reaction equation
[CH3:1][C:2]1[C:3]([C:7]([OH:9])=O)=[CH:4][NH:5][CH:6]=1.Cl.[CH2:11]([O:13][C:14](=[O:18])[CH2:15][CH2:16][NH2:17])[CH3:12].C(N(CC)CC)C.Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl>[CH3:1][C:2]1[C:3]([C:7]([NH:17][CH2:16][CH2:15][C:14]([O:13][CH2:11][CH3:12])=[O:18])=[O:9])=[CH:4][NH:5][CH:6]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2744084-Methyl-1H-pyrrole-3-carboxylic acidHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 12146427Ethyl 3-(4-methyl-3-pyrrolecarboxamido)propionateYield 43.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using 7.63 g (60 mmol) of 4-methyl-3-pyrrolecarboxylic acid, 15.4 g (100 mmol) of β-alanine ethyl ester hydrochloride, 14 ml (100 mmol) of triethylamine, 17.3 g (90 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 100 ml of methylene chloride, 5.80 g of the title compound were obtained in a similar manner as in Example 2 (yield: 26%).

Sources & evidence

ORD record
ord-dce44ebee5b44e60a064c654d01eafc2
Source dataset
uspto-grants-2004_03
Patent number
US06713634B2

Linked notes

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