Triethylamine → Benzyl 3-(3-pyrrolecarboxamido)propionate

HRID 322610Notes

Reaction equation

HRID 322610 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[CH:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:20]([O:27][C:28](=[O:32])[CH2:29][CH2:30][NH2:31])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.P(C#N)(=O)(OCC)OCC.C(N(CC)CC)C>CN(C)C=O>[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:31][CH2:30][CH2:29][C:28]([O:27][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:32])=[O:8])=[CH:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 101030Pyrrole-3-carboxylic acidHCID 135021004-Methylbenzene-1-sulfonic acid--benzyl beta-alaninate (1/1)

Product 1

HCID 10516322Benzyl 3-(3-pyrrolecarboxamido)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Into a solution of 1.67 g (15 mmol) of 3-pyrrole-carboxylic acid and 6.33 g (18 mmol) of β-alanine benzyl ester p-toluenesulfonate in 20 ml of dimethylformamide, a solution of 2.94 g (18 mmol) of diethyl phosphorocyanidate in 10 ml of dimethylformamide was added dropwise under ice cooling and stirring. A solution of 3.64 g (36 mmol) of triethylamine in 20 ml of dimethylformamide was then added dropwise. The reaction mixture was stirred at 0° C. for 1 hour and then at room temperature for 24 hours.

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 1 hour

Sources & evidence

ORD record
ord-1ed1883e187c49cb902e55e4052de794
Source dataset
uspto-grants-2001_04
Patent number
US06211362B1

Reaction notes

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