Potassium Hydroxide → 3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)-amino]-propionic acid

HRID 29780Notes

Reaction equation

HRID 29780 reaction equation
C([O:3][C:4](=[O:17])[CH2:5][CH2:6][NH:7][C:8]([C:10]1[NH:11][C:12]([Br:16])=[C:13]([Br:15])[CH:14]=1)=[O:9])C.[OH-].[K+]>O1CCOCC1.O>[Br:15][C:13]1[CH:14]=[C:10]([C:8]([NH:7][CH2:6][CH2:5][C:4]([OH:17])=[O:3])=[O:9])[NH:11][C:12]=1[Br:16]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 686374643-[(4,5-dibromo-1H-pyrrole-2-carbonyl)-amino]-propionic acid ethyl ester

Product 1

HCID 686366043-[(4,5-dibromo-1H-pyrrole-2-carbonyl)-amino]-propionic acid

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

To a solution of 3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)-amino]-propionic acid ethyl ester (7.80 g, 21.1 mmol) in 160 mL of 1:1 mixture of dioxane-H2O is added KOH (4.72 g, 84.2 mmol). The mixture is stirred at room temperature overnight. The solution is extracted with Et2O (100 mL) and the aqueous layer is then acidified with HCl to a pH of less than 2 followed by extraction with EtOAc (80 mL×3). The EtOAc layers are combined, washed with brine, and dried with Na2SO4. After removal of solvent, 3-[(4,5-dibromo-1H-pyrrole-2-carbonyl)-amino]-propionic acid is obtained. It was used without further purification; 1H NMR (DMSO-d6) δ 2.47 (t, 2H, J=7.2 Hz), 3.39 (q, 2H, J=6.0 Hz), 6.90 (s, 1H), 8.17 (t, 1H, J=4.8 Hz); m/z [M++1] 340.9.

Workup

  1. extractionThe solution is extracted with Et2O (100 mL)
  2. extractionfollowed by extraction with EtOAc (80 mL×3)
  3. washwashed with brine
  4. dry with materialdried with Na2SO4
  5. customAfter removal of solvent

Sources & evidence

ORD record
ord-e28ef68b22fc429f99dfa9b14d3c3027
Source dataset
uspto-grants-2008_09
Patent number
US07423031B2

Reaction notes

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