DL-norvaline → 2-(1H-Pyrrol-1-YL)pentanoic acid

Reaction equation

[NH2:1][CH:2]([CH2:6][CH2:7][CH3:8])[C:3]([OH:5])=[O:4].C([O-])(=O)C.[Na+].CO[CH:16]1[CH2:20][CH2:19][CH:18](OC)O1>C(O)(=O)C>[N:1]1([CH:2]([CH2:6][CH2:7][CH3:8])[C:3]([OH:5])=[O:4])[CH:16]=[CH:20][CH:19]=[CH:18]1

Participants

Procedure

2-Aminopentanoic acid (0.2 mole) is added to a solution of sodium acetate (0.2 mole) in about 300 ml of glacial acetic acid. This solution is heated to effect solution and is then refluxed for 5 minutes. To the refluxing solution is added (0.2 mole) 2.5-dimethoxytetrahydrofuran as quickly as possible. The mixture is refluxed for a further 2 minutes and the acetic acid is flash evaporated. The residue is taken up in ethyl acetate, washed with water, dried and the solvent removed under vacuo to give 2-(1-pyrryl)pentanoic acid.