Acetic Acid → HCID 19955607, compound

HRID 1779448Notes

Reaction equation

HRID 1779448 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[C:31](=[O:32])[C:30](=[O:33])[C:29]=3[O:34]C(C)C)=[CH:18][CH:17]=2)[C:7]([C:11]([O:13][CH3:14])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].C(O)(=O)C>O>[CH2:1]([C:5]1[N:6]([CH2:15][C:16]2[CH:17]=[CH:18][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]3[C:29](=[O:34])[C:30](=[O:33])[C:31]=3[OH:32])=[CH:20][CH:21]=2)[C:7]([C:11]([O:13][CH3:14])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 19955590HCID 19955590, compound

Product 1

HCID 19955607HCID 19955607, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Methyl 2-butyl-4-chloro-1-[2'-(2-isopropoxy-3,4-dioxocyclobut-1-en-1-yl)biphenyl-4-ylmethyl]-1H-imidazole-5-carboxylate (0.26 g; preparable as described in Example 27(c)) was heated in a mixture of glacial acetic acid (5 ml) and water (5 ml) at 95°-100° C. for 5 hours. The solvents were evaporated in vacuo and the residue obtained was purified by flash chromatography on silica gel (eluting with 10% rising to 30% industrial methylated spirit in ethyl acetate) to give methyl 2-butyl-4-chloro-1-[2'-(2-hydroxy-3,4-dioxo-cyclobut-1-en-1-yl)biphenyl-4-ylmethyl]-1H-imidazole-5-carboxylate, an active compound of the present invention, as a yellow oil (0.1 g).

Workup

  1. customThe solvents were evaporated in vacuo
  2. customthe residue obtained
  3. customwas purified by flash chromatography on silica gel (eluting with 10% rising to 30% industrial methylated spirit in ethyl acetate)

Sources & evidence

ORD record
ord-a12ea1c1de1643c7951c4018e964ece2
Source dataset
uspto-grants-1997_05
Patent number
US05627191

Reaction notes

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