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

HRID 872188Notes

Reaction equation

HRID 872188 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. Aqueous 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. extractionAqueous layer was extracted with AcOEt
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5f6e0209e8ca41d2907a512e833afbc6
Source dataset
uspto-grants-2015_03
Patent number
US08975267B2

Reaction notes

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