Hydrochloric Acid → HCID 86746552, compound

HRID 2081884Notes

Reaction equation

HRID 2081884 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[C:25]([O:33]COC)[CH:24]=2)[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)/[C:12]([O:14][CH3:15])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].Cl>CO>[CH2:1]([C:5]1[N:6]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[C:25]([OH:33])[CH:24]=2)[C:7](/[CH:10]=[C:11](\[CH2:16][C:17]2[S:18][CH:19]=[CH:20][CH:21]=2)/[C:12]([O:14][CH3:15])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86746553HCID 86746553, compound

Product 1

HCID 86746552HCID 86746552, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl (E)-3-[2-n-butyl-1-{(4-carbomethoxy-3-methoxymethoxyphenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoate (2.1 g, 4.1 mmol) in 40 mL of methanol was added approximately 0.1 mL of concentrated hydrochloric acid. The reaction was refluxed for 5 hours and then concentrated in vacuo. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The layers were separated. The organic extract was dried with magnesium sulfate, and the solvent was removed in vacuo to give 1.76 g (92%) of product as an oil.

Workup

  1. temperatureThe reaction was refluxed for 5 hours
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. customThe layers were separated
  5. extractionThe organic extract
  6. dry with materialwas dried with magnesium sulfate
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-549c7bc5f96a45979db2872d435798b1
Source dataset
uspto-grants-1993_02
Patent number
US05185351

Reaction notes

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