Water → HCID 9934043, compound

HRID 378340Notes

Reaction equation

HRID 378340 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:9][C@@H:10]([C:34]([O:36]CC)=[O:35])[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][C@H:19]([C:29]([O:31]CC)=[O:30])[NH:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[CH:14][CH:13]=1)=[O:8].[OH-].[Na+].O>O1CCOCC1.CCO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:9][C@@H:10]([C:34]([OH:36])=[O:35])[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][C@H:19]([C:29]([OH:31])=[O:30])[NH:20][C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=2)=[O:22])=[CH:16][CH:17]=1)=[O:8]

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 10896596HCID 10896596, compound

Product 1

HCID 9934043HCID 9934043, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a cooled (0° C.) solution of 1,4-bis-(2-(2-pyridylcarbonylamino)-2-ethyloxycarbonyl-(2R)-ethyl)-benzene (1.40 g; 2.70 mmol) in dioxane (4 ml) and EtOH (4 ml) an aqueous 2N NaOH solution (4 ml, 8.0 mmol) and water (2 ml) was added. The mixture was allowed to come to r.t. overnight. The solution was concentrated to approximately 5 ml under reduced pressure and the pH of the residual solution was adjusted to pH 3 by addition of aqueous 4N HCl, whereupon an oil separated. The mixture was extracted with ethyl acetate (3×15 ml). The combined organic layer was dried (MgSO4), concentrated and the residue purified by: flash chromatography (chloroform/MeOH/HOAc 8/2/1) to yield 1,4-Bis-(2-(2-pyridylcarbonylamino)-2-carboxy-(2R)-ethyl)-benzene (1.1 g, 70%).

Workup

  1. additionwas added
  2. concentrationThe solution was concentrated to approximately 5 ml under reduced pressure
  3. additionthe pH of the residual solution was adjusted to pH 3 by addition of aqueous 4N HCl, whereupon an oil
  4. customseparated
  5. extractionThe mixture was extracted with ethyl acetate (3×15 ml)
  6. dry with materialThe combined organic layer was dried (MgSO4)
  7. concentrationconcentrated
  8. customthe residue purified by: flash chromatography (chloroform/MeOH/HOAc 8/2/1)

Sources & evidence

ORD record
ord-b673cc3140554e6ab68b9a1fc757e47f
Source dataset
uspto-grants-2000_02
Patent number
US06030989

Reaction notes

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