Water → 2,3,4,5-Tetraiodopyrrol-1-acetic acid

HRID 1081952Notes

Reaction equation

HRID 1081952 reaction equation
C([O:3][C:4](=[O:15])[CH2:5][N:6]1[C:10]([I:11])=[C:9]([I:12])[C:8]([I:13])=[C:7]1[I:14])C.O.[OH-].[Na+]>O1CCOCC1>[I:14][C:7]1[N:6]([CH2:5][C:4]([OH:15])=[O:3])[C:10]([I:11])=[C:9]([I:12])[C:8]=1[I:13]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 539447922,3,4,5-Tetraiodopyrrol-1-acetic acid ethyl ester

Product 1

HCID 233633512,3,4,5-Tetraiodopyrrol-1-acetic acidYield 96.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

TO a solution of 23.2 g of compound B), 2,3,4,5-tetraiodopyrrol-1-acetic acid ethyl ester (35.32 mmol) , in 840 mL of a dioxane (750 mL) / H2O (90 mL) mixture, 36 mL of 1M NaOH (36 mmol) are quickly added (10 min) and the final solution is kept at room temperature for 4 h. The reaction mixture is treated with carbon Carbopuron 4N, filtered, then acidified with 37% HC1 (w/w) and diluted in 500 1 of H2O, to give a solid which is filtered and purified by chromatography (silica gel (product E. Merck item 9385): eluent: CHCl3 : MeOH : 25% NH4OH (w/w) =7.5:2:0.3 (v/v/v)). Fractions with similar purity are collected, evaporated and diluted with 200 mL of H2O. By acidifying the aqueous phase with 40 mL of 1M HCl , a solid precipitates, which is filtered, washed with H2O and dried under reduced pressure. 21.5 g of 2,3,4,5-tetraiodopyrrol-1-acetic acid(34.20 mmol) are obtained.

Workup

  1. additionThe reaction mixture is treated with carbon Carbopuron 4N
  2. filtrationfiltered
  3. additiondiluted in 500 1 of H2O
  4. customto give a solid which
  5. filtrationis filtered
  6. custompurified by chromatography (silica gel (product E. Merck item 9385): eluent: CHCl3 : MeOH : 25% NH4OH (w/w) =7.5:2:0.3 (v/v/v))
  7. customFractions with similar purity are collected
  8. customevaporated
  9. additiondiluted with 200 mL of H2O
  10. customa solid precipitates
  11. filtrationwhich is filtered
  12. washwashed with H2O
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-1fe8a550415a4698bd39bbf432b8b65d
Source dataset
uspto-grants-1996_12
Patent number
US05587487

Reaction notes

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