Sodium Hydroxide → 2-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(2-fluoroethylthio)-1H-imidazole-5-carboxylic acid

HRID 2292686Notes

Reaction equation

HRID 2292686 reaction equation
[OH-].[Na+].[CH2:3]([C:7]1[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([OH:36])=[O:35])=[CH:24][CH:23]=2)[C:9]([C:16]([O:18]CC)=[O:17])=[C:10]([S:12][CH2:13][CH2:14][F:15])[N:11]=1)[CH2:4][CH2:5][CH3:6]>C(O)C>[CH2:3]([C:7]1[N:8]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([OH:36])=[O:35])=[CH:26][CH:27]=2)[C:9]([C:16]([OH:18])=[O:17])=[C:10]([S:12][CH2:13][CH2:14][F:15])[N:11]=1)[CH2:4][CH2:5][CH3:6]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 21479014HCID 21479014, compound

Product 1

HCID 214790602-butyl-1-[[2'-carboxy-(1,1'-biphenyl)-4-yl]-methyl]-4-(2-fluoroethylthio)-1H-imidazole-5-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.25 cm3 of a 2N solution of sodium hydroxide is added at ambient temperature to 450 mg of the product obtained in Example 43 dissolved in 10 cm3 of ethanol, then the mixture is left for 3 days. The solvents are evaporated under reduced pressure, the residue is taken up in water, 2.25 cm3 of hydrochloric acid 2M/1 is added. The precipitate formed is filtered, washed with water, dried under reduced pressure and 380 mg of expected product is obtained which is recrystallized from isopropanol. M.p.=185°-186° C.

Workup

  1. customThe solvents are evaporated under reduced pressure
  2. addition2.25 cm3 of hydrochloric acid 2M/1 is added
  3. customThe precipitate formed
  4. filtrationis filtered
  5. washwashed with water
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-09224e8569e6445397364e6aef546c5e
Source dataset
uspto-grants-1997_11
Patent number
US05684028

Reaction notes

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