Hydrochloric Acid → 3-(2-Benzyloxycarbonylpyrrol-1-yl)benzoic acid

HRID 399820Notes

Reaction equation

HRID 399820 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]([C:13]1[N:14]([C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([O:23]C)=[O:22])[CH:15]=[CH:16][CH:17]=1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O1CCOCC1.Cl>O.C(OCC)(=O)C>[CH2:3]([O:10][C:11]([C:13]1[N:14]([C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21]([OH:23])=[O:22])[CH:15]=[CH:16][CH:17]=1)=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 18945465Methyl 3-(2-benzyloxycarbonylpyrrol-1-yl)benzoate

Product 1

HCID 189453413-(2-Benzyloxycarbonylpyrrol-1-yl)benzoic acidYield 50.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1N-Sodium hydroxide solution (1.5 ml) was added to a mixture of methyl 3-(2-benzyloxycarbonylpyrrol-1-yl)benzoate (0.5 g) and dioxane (20 ml), and the mixture was stirred for 3 days at ambient temperature. The reaction mixture was poured into the mixture of ethyl acetate and water and the separated aqueous layer was adjusted to pH 1 with 6N-hydrochloric acid. The mixture was extracted with ethyl acetate and extract was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was triturated with n-hexane to give 3-(2-benzyloxycarbonylpyrrol-1-yl)benzoic acid (0.24 g).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. extractionextract
  3. washwas washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by concentration
  6. customthe residue was triturated with n-hexane

Sources & evidence

ORD record
ord-e86ac1fc5fd84afd8327dc1ea33c1f1d
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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