Pyridine → 2-ethoxy-1-(ethoxymethyl)ethyl 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1h-imidazole-1-carboxylate

HRID 1985889Notes

Reaction equation

HRID 1985889 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]([C:11]1[NH:12][CH:13]=[CH:14][N:15]=1)[CH3:10].N1C=CC=CC=1.[C:22](Cl)(Cl)=[O:23].[CH2:26]([O:28][CH2:29][CH:30]([OH:35])[CH2:31][O:32][CH2:33][CH3:34])[CH3:27].C(=O)([O-])O.[Na+]>ClCCl>[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]([C:11]1[N:15]([C:22]([O:35][CH:30]([CH2:31][O:32][CH2:33][CH3:34])[CH2:29][O:28][CH2:26][CH3:27])=[O:23])[CH:14]=[CH:13][N:12]=1)[CH3:10]

Participants

7

Reactant 5

HCID 1049PyridineHCID 6371PhosgeneHCID 776641,3-Diethoxy-2-propanolHCID 516892Sodium BicarbonateHCID 24738933Demiditraz

Product 1

HCID 577183812-ethoxy-1-(ethoxymethyl)ethyl 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1h-imidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of Example 58 (500 mg, 2.5 mmol) and pyridine (0.44 ml, 5.5 mmol) in anhydrous dichloromethane (5 ml), at 0° C. and under nitrogen, was added phosgene (20% in toluene, 1.44 ml, 2.75 mmol). The mixture was stirred at 0° C. for 20 min, before addition of 1,3-diethoxypropan-2-ol (407 mg, 2.75 mmol). The reaction mixture was stirred at room temperature for 30 min and then poured into ice water (10 ml). The mixture was adjusted to pH 7 by addition of solid sodium hydrogen carbonate and the two layers were separated. The aqueous phase was extracted with dichloromethane (2×10 ml) and the combined extracts were dried (MgSO4) and concentrated in vacuo.

Workup

  1. customthe two layers were separated
  2. extractionThe aqueous phase was extracted with dichloromethane (2×10 ml)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d1c56fe0c9c4479bc1117dec8746052
Source dataset
uspto-grants-2009_06
Patent number
US07547718B2

Reaction notes

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