Hydrochloric Acid → 4-(4-(ethoxycarbonyl)-5-methyl-1H-pyrrol-3-yl)butanoic acid

HRID 872189Notes

Reaction equation

HRID 872189 reaction equation
Cl.[NH2:2][CH2:3][C:4](=O)[CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=O.C(O[Na])(C)=O.Cl>O>[CH2:19]([O:18][C:12]([C:13]1[C:4]([CH2:5][CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:3][NH:2][C:14]=1[CH3:16])=[O:17])[CH3:20]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8868Ethyl AcetoacetateHCID 713866726-Amino-5-oxohexanoic acid hydrochlorideHCID 178418247HCID 178418247, compound

Product 1

HCID 593760204-(4-(ethoxycarbonyl)-5-methyl-1H-pyrrol-3-yl)butanoic acidYield 70.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6-amino-5-oxohexanoic acid hydrochloride (9.73 g, 49.8 mmol) was dissolved in H2O (35 mL), and ethyl acetoacetate (5.51 g, 42.34 mmol) and AcONa (20.3 g, 14.95 mmol) were added to the above-mentioned solution. The reaction solution was refluxed for 1 h, cooled to room temperature and 0.5N HCl was added until a pH of about 5 was reached. The combined organic layers were anidrified on Na2SO4, filtered and concentrated to give 7.15 g (yield: 60%) of the title compound as brown solid.

Workup

  1. temperatureThe reaction solution was refluxed for 1 h
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-839c2f56d6194051b0613409d015f885
Source dataset
uspto-grants-2015_03
Patent number
US08975267B2

Reaction notes

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