Triethylamine → Benzyl 3-(1-methyl-3-pyrrolecarboxamido)propionate

HRID 51233Notes

Reaction equation

HRID 51233 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([OH:9])=O)=[CH:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:21]([O:28][C:29](=[O:33])[CH2:30][CH2:31][NH2:32])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.P(C#N)(=O)(OCC)OCC.C(N(CC)CC)C>CN(C)C=O>[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([C:7]([NH:32][CH2:31][CH2:30][C:29]([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:33])=[O:9])=[CH:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 101540541-methyl-1H-pyrrole-3-carboxylic acidHCID 135021004-Methylbenzene-1-sulfonic acid--benzyl beta-alaninate (1/1)

Product 1

HCID 10803123Benzyl 3-(1-methyl-3-pyrrolecarboxamido)propionate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent4×

Procedure

Into a solution of 5.01 g (40 mmol) of 1-methyl-3-pyrrolecarboxylic acid and 16.87 g (48 mmol) of β-alanine benzyl ester p-toluenesulfonate in 200 ml of dimethylformamide (hereinafter called “DMF”), a solution of 7.83 g (48 mmol) of diethyl phosphorocyanidate in 50 ml of DMF was added dropwise under ice cooling and stirring. A solution of 9.71 g (96 mmol) of triethylamine in 50 ml of DMF was then added dropwise, and the reaction mixture was stirred at room temperature for 67 hours.

Workup

  1. additionwas added dropwise under ice cooling
  2. stirringthe reaction mixture was stirred at room temperature for 67 hours

Sources & evidence

ORD record
ord-d53e4bae2e6f4ad89e1f9e1891bf3e97
Source dataset
uspto-grants-2004_03
Patent number
US06713634B2

Reaction notes

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