p-Toluenesulfonic acid → Methyl 5-(5-methoxy-1,4,5,6-tetrahydrocyclopenta[d]imidazol-2-yl)-2,4-dimethylbenzoate

HRID 541469Notes

Reaction equation

HRID 541469 reaction equation
O[C:2]12[CH2:21][CH:20]([O:22][CH3:23])[CH2:19][CH:3]1[NH:4][C:5]([C:7]1[C:8]([CH3:18])=[CH:9][C:10]([CH3:17])=[C:11]([CH:16]=1)[C:12]([O:14][CH3:15])=[O:13])=[N:6]2.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C)C=O>[CH3:23][O:22][CH:20]1[CH2:21][C:2]2[NH:6][C:5]([C:7]3[C:8]([CH3:18])=[CH:9][C:10]([CH3:17])=[C:11]([CH:16]=3)[C:12]([O:14][CH3:15])=[O:13])=[N:4][C:3]=2[CH2:19]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 178497309HCID 178497309, compound2×

Product 1

HCID 68288254Methyl 5-(5-methoxy-1,4,5,6-tetrahydrocyclopenta[d]imidazol-2-yl)-2,4-dimethylbenzoateYield 87.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into around-bottom flask, was placed a solution of methyl 5-(3a-hydroxy-5-methoxy-1,3a,4,5,6,6a-hexahydrocyclopenta[d]imidazol-2-yl)-2,4-dimethylbenzoate (compound 461.5, 200 mg, 0.38 mmol, 1.00 equiv, 60%) in N,N-dimethylformamide (mL). p-Toluenesulfonic acid (20 mg, 0.12 mmol, 0.18 equiv) was added and the resulting solution was stiffed overnight at 80° C., then concentrated in vacuo. The residue was purified by silica gel chromatography with dichloromethane/methanol (10:1) as the eluent to obtain the title compound as a brown oil (100 mg, 66%).

Workup

  1. customInto around-bottom flask, was placed
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by silica gel chromatography with dichloromethane/methanol (10:1) as the eluent

Sources & evidence

ORD record
ord-9aba82a9eaf148ceac5e51d201e09339
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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