Hydrochloric Acid → 4-[4-(methoxycarbonyl)-1H-pyrrol-3-yl]butanoic acid

HRID 626866Notes

Reaction equation

HRID 626866 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][CH2:5][CH2:6][C:7]1[C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][NH:10][CH:11]=1.[Li+].[OH-].Cl>O1CCOCC1.O.CCOC(C)=O>[CH3:15][O:14][C:12]([C:8]1[C:7]([CH2:6][CH2:5][CH2:4][C:3]([OH:16])=[O:2])=[CH:11][NH:10][CH:9]=1)=[O:13]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68276464methyl 4-(4-methoxy-4-oxobutyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 682765264-[4-(methoxycarbonyl)-1H-pyrrol-3-yl]butanoic acidYield 99%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-(4-methoxy-4-oxobutyl)-1H-pyrrole-3-carboxylate (50 mg, 0.220 mmol) was suspended in anhydrous dioxane (2 mL) and H2O (0.5 mL) and LiOH (5.3 mg, 0.220 mmol) was added. The reaction mixture was stirred at room temperature for 4 h. Reaction solution was acidified with 1N HCl and AcOEt (50 mL) and H2O (20 mL) were added. Acqueous layer was extracted with AcOEt and the combined organic layers anidrified on Na2SO4, filtered and concentrated to give 46 mg (quantitative yield) of the title compound as a white solid.

Workup

  1. customReaction solution
  2. additionwere added
  3. extractionAcqueous layer was extracted with AcOEt
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d9814eda6e274ea58d6cc5197103c8af
Source dataset
uspto-grants-2016_04
Patent number
US09309253B2

Reaction notes

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