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

HRID 1737244Notes

Reaction equation

HRID 1737244 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-1521e569c997403d8a3e4f6283b8f035
Source dataset
uspto-grants-1999_10
Patent number
US05962448

Reaction notes

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