HCID 86750789, compound → HCID 19955598, compound

HRID 1779451Notes

Reaction equation

HRID 1779451 reaction equation
[CH2:1](/[C:8](=[CH:13]\[C:14]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[C:29](=[O:30])[C:28](=[O:31])[C:27]=3[O:32]C(C)C)=[CH:22][CH:21]=2)[C:17]([CH2:36][CH2:37][CH2:38][CH3:39])=[N:16][C:15]=1[Cl:40])/[C:9]([O:11]C)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C>[CH2:1](/[C:8](=[CH:13]\[C:14]1[N:18]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[C:27](=[O:32])[C:28](=[O:31])[C:29]=3[OH:30])=[CH:22][CH:21]=2)[C:17]([CH2:36][CH2:37][CH2:38][CH3:39])=[N:16][C:15]=1[Cl:40])/[C:9]([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86750789HCID 86750789, compound

Product 1

HCID 19955598HCID 19955598, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of (E)-methyl 2-benzyl-3-[2-butyl-4-chloro-1-[4-(2-isopropoxy-3,4-dioxocyclobut-1-en-1-yl)benzyl]-1H-imidazol-5-yl ]propenoate (1.2 g; preparable as described in Example 30(d)) and aqueous acetic acid (50%; 20 ml) was heated at 95°-100° C. for 6 hours. The solvents were evaporated under reduced pressure and the residue obtained was triturated with diethyl ether (2 ×20 ml). The resulting solid was dissolved in industrial methylated spirit (20 ml). Aqueous sodium hydroxide solution (0.5M, 22 ml) was added and the resulting mixture was stirred for 1 hour at ambient temperature and neutralised with hydrochloric acid (5M). The solvent was evaporated under reduced pressure and the residue obtained was extracted with aqueous sodium hydroxide solution (1M; 60 ml) and then acidified with hydrochloric acid (5M). The resulting precipitate was collected, washed with water (2×10 ml) and then dried to give (E)-2-benzyl-3-[2-butyl-4-chloro-1-[4-(2-hydroxy-3,4-dioxocyclobut-1 -en-1-yl)benzyl]-1H-imidazol-5-yl]propenoic acid, an active compound of the present invention, as a solid (0.54 g; m.p. 155°-160° C.).

Workup

  1. temperaturewas heated at 95°-100° C. for 6 hours
  2. customThe solvents were evaporated under reduced pressure
  3. customthe residue obtained
  4. customwas triturated with diethyl ether (2 ×20 ml)
  5. dissolutionThe resulting solid was dissolved in industrial methylated spirit (20 ml)
  6. additionAqueous sodium hydroxide solution (0.5M, 22 ml) was added
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue obtained
  9. extractionwas extracted with aqueous sodium hydroxide solution (1M; 60 ml)
  10. customThe resulting precipitate was collected
  11. washwashed with water (2×10 ml)
  12. customdried

Sources & evidence

ORD record
ord-c16662b1fc5345a88d75980b962c0684
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

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