p-Toluenesulfonic acid → Methyl 3-[5-(hydroxymethyl)-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate

HRID 15417Notes

Reaction equation

HRID 15417 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:14]([CH:15]([C:21]2[CH:26]=[CH:25][C:24]([C:27]#[N:28])=[CH:23][CH:22]=2)[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:13]=[N:12][CH:11]=1)(C(C)(C)C)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:8][CH2:9][C:10]1[N:14]([CH:15]([C:21]2[CH:22]=[CH:23][C:24]([C:27]#[N:28])=[CH:25][CH:26]=2)[CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH:13]=[N:12][CH:11]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 68695105Methyl 3-[5-(t-butyl-dimethylsilanyloxymethyl)-imidazole-1-yl]-3-(4-cyanophenyl)-propionate

Product 1

HCID 17975627Methyl 3-[5-(hydroxymethyl)-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title A compound, methyl 3-[5-(t-butyl-dimethylsilanyloxymethyl)-imidazole-1-yl]-3-(4-cyanophenyl)-propionate (0.98 g, 2.46 mmol) and p-toluenesulfonic acid (0.55 g, 2.9 mmol) are stirred in MeOH (10 mL) at RT for 24 h. The reaction mixture is evaporated to an oil and partitioned between EtOAc and aqueous saturated sodium bicarbonate. The combined organic phases are dried over anhydrous sodium sulfate and removal of the solvent in vacuo yields methyl 3-[5-(hydroxymethyl)-imidazol-1-yl]-3-(4-cyano-phenyl)-propionate as an oil: 1H-NMR (CDCl3) δ 7.65 (2H, d, J=8.4), 7.62 (1H, s), 7.31 (2H, d, J=8.4), 6.98 (1H, s), 6.05 (1H, dd, J=9.2, 6.2), 4.62 (1H, d, J=13.5), 4.47 (1H, d, J=13.5), 3.67 (3H, s), 3.36 (1H, dd, J=16.5, 9.2), 3.21 (1H, dd, J=16.5, 6.2); e/z (ES) 286 (M+1, 100%).

Workup

  1. customThe reaction mixture is evaporated to an oil
  2. custompartitioned between EtOAc and aqueous saturated sodium bicarbonate
  3. dry with materialThe combined organic phases are dried over anhydrous sodium sulfate and removal of the solvent in vacuo

Sources & evidence

ORD record
ord-19f1badb0526496eb7446ade120ca37b
Source dataset
uspto-grants-2010_06
Patent number
US07732603B2

Reaction notes

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