Hydrochloric Acid → 5-(1H-imidazol-1-yl)pentanoic acid

HRID 870577Notes

Reaction equation

HRID 870577 reaction equation
[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12]C)=[O:11])[CH:5]=[CH:4][N:3]=[CH:2]1.[OH-].[Li+].Cl>O1CCCC1.O>[N:1]1([CH2:6][CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 54266609Methyl 5-imidazol-1-ylpentanoate

Product 1

HCID 128033135-(1H-imidazol-1-yl)pentanoic acidYield 130.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Stir a solution of methyl 5-imidazol-1-ylpentanoate (0.60 g; 1.0 equiv; 3.29 mmoles) and lithium hydroxide (0.553 g; 4 equiv; 13.17 mmoles) in tetrahydrofuran (20 mL) and water (15 mL) for 18 hours. Add 3 ml of 5N hydrochloric acid then concentrate the mixture. Purify the crude product by column chromatography (0 to 15% methanol in dichloromethane) to afford 5-imidazol-1-ylpentanoic acid (0.72 g; 19%) as a yellow oil: MS (m/z): 169(M+1).

Workup

  1. concentrationthen concentrate the mixture
  2. customPurify the crude product by column chromatography (0 to 15% methanol in dichloromethane)

Sources & evidence

ORD record
ord-f266ef17be58499186ba1259e1867ca5
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

Loading…