Sodium Hydroxide → 1-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxylic acid

HRID 278500Notes

Reaction equation

HRID 278500 reaction equation
[CH2:1]([O:8][C@H:9]([C@H:11]([N:24]1[CH:28]=[C:27]([C:29]([O:31]C)=[O:30])[N:26]=[CH:25]1)[CH2:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[CH2:1]([O:8][C@H:9]([C@H:11]([N:24]1[CH:28]=[C:27]([C:29]([OH:31])=[O:30])[N:26]=[CH:25]1)[CH2:12][CH2:13][C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]=[CH:16][CH:15]=1)[CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 69690219methyl 1-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxylate

Product 1

HCID 573122811-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxylic acidYield 90.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of methyl 1-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)- 3-pentyl]imidazole-4-carboxylate (obtained in Example 3(20))(97 mg) and sodium hydroxide (12 mg) in ethanol (2 ml) and water (0.2 ml) was stirred at room temperature overnight. The solvent was evaporated and the residue was taken up in a mixture of ethyl acetate and water. The aqueous layer was separated, acidified to pH 3 with hydrochloric acid, and extracted with ethyl acetate. The extract was dried and evaporated to give a pale brown powder of 1-[(2S,3R)-2-benzyloxy-5-(1-naphthyl)-3-pentyl]imidazole-4-carboxylic acid (84.5 mg).

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was taken up in a mixture of ethyl acetate and water
  3. customThe aqueous layer was separated
  4. extractionextracted with ethyl acetate
  5. customThe extract was dried
  6. customevaporated

Sources & evidence

ORD record
ord-98596e712745458195cc3515f9137f93
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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