Sodium Hydroxide → 2-butyl-3-[5-(1-carboxycyclopent-3-enyl)thiophen-2-ylmethyl]-5-chloro-3H-imidazole-4-carboxylic acid

HRID 481416Notes

Reaction equation

HRID 481416 reaction equation
C([O:3][C:4]([C:6]1[N:7]([CH2:16][C:17]2[S:18][C:19]([C:22]3([C:27]([O:29]CC)=[O:28])[CH2:26][CH:25]=[CH:24][CH2:23]3)=[CH:20][CH:21]=2)[C:8]([CH2:12][CH2:13][CH2:14][CH3:15])=[N:9][C:10]=1[Cl:11])=[O:5])C.[OH-].[Na+]>CO>[CH2:12]([C:8]1[N:7]([CH2:16][C:17]2[S:18][C:19]([C:22]3([C:27]([OH:29])=[O:28])[CH2:26][CH:25]=[CH:24][CH2:23]3)=[CH:20][CH:21]=2)[C:6]([C:4]([OH:5])=[O:3])=[C:10]([Cl:11])[N:9]=1)[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 700851902-butyl-5-chloro-3-[5-(1-ethoxycarbonylcyclopent-3-enyl)thiophen-2-ylmethyl]-3H-imidazole-4-carboxylic acid ethyl ester2×

Product 1

HCID 190662892-butyl-3-[5-(1-carboxycyclopent-3-enyl)thiophen-2-ylmethyl]-5-chloro-3H-imidazole-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the product of Step 1, above (71) (50 mg) in 2 ml of methanol was added 1 ml 2N NaOH. This mixture was stirred at ambient temperature for 2 hours, the solvent was removed and the residue taken up in water and extracted (2×EtOAc). The aqueous layer was then acidified with 10% HCl and extracted (3×EtOAc). The combined organics were dried over MgSO4, filtered and concentrated to dryness to yield the title compound (72).

Workup

  1. customthe solvent was removed
  2. extractionextracted (2×EtOAc)
  3. extractionextracted (3×EtOAc)
  4. dry with materialThe combined organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dcc456adb6ad41c882c9532a9b255d01
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Reaction notes

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