HCID 13228943, compound → HCID 13228938, compound

HRID 1380546Notes

Reaction equation

HRID 1380546 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18]CC3C=CC=CC=3)=[C:14]([CH3:26])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[N:3]=[C:4]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:5]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[C:14]([CH3:26])[CH:13]=2)[C:6]=1[CH2:7][C:8]([OH:10])=[O:9]

Participants

3

Reactant 1

HCID 13228943HCID 13228943, compound

Product 1

HCID 13228938HCID 13228938, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-Chloro-1-(4-benzyloxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid (20 g) was boiled in 200 ml of trifluoroacetic acid for 30 minutes. The reaction mixture was evaporated to dryness under reduced pressure and the residue was dissolved in 300 ml of diethyl ether and washed with two 300-ml portions of water. The diethyl ether layer was extracted with six 150-ml portions of 0.3 N-sodium hydroxide. The aqueous layers containing the desired product were combined, adjusted to pH 2 with hydrochloric acid and extracted with four 200-ml portions of ethyl acetate. The ethyl acetate layer was evaporated to dryness under reduced pressure and the residue was dissolved in 20 ml of acetone, followed by addition of 30 ml of diethyl ether to give 10 g or 4-chloro-1-(4-hydroxy-3-methylbenzyl)-2-phenylimidazole-5-acetic acid as colorless needles, m.p. 193°-195° C. (decompn.).

Workup

  1. customThe reaction mixture was evaporated to dryness under reduced pressure
  2. dissolutionthe residue was dissolved in 300 ml of diethyl ether
  3. washwashed with two 300-ml portions of water
  4. extractionThe diethyl ether layer was extracted with six 150-ml portions of 0.3 N-sodium hydroxide
  5. additionThe aqueous layers containing the desired product
  6. extractionextracted with four 200-ml portions of ethyl acetate
  7. customThe ethyl acetate layer was evaporated to dryness under reduced pressure
  8. dissolutionthe residue was dissolved in 20 ml of acetone
  9. additionfollowed by addition of 30 ml of diethyl ether

Sources & evidence

ORD record
ord-bc47aed3866142f0bf8091a565d82589
Source dataset
uspto-grants-1986_04
Patent number
US04582847

Reaction notes

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