Triethylamine → isobutyl 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1h-imidazole-1-carboxylate

HRID 734462Notes

Reaction equation

HRID 734462 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].C(N(CC)CC)C.Cl[C:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25]>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:24]([O:26][CH2:27][CH:28]([CH3:30])[CH3:29])=[O:25])[CH:14]=[CH:13][N:12]=1)[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 24738933Demiditraz

Product 1

HCID 57718424isobutyl 2-[(1S)-1-(2,3-dimethylphenyl)ethyl]-1h-imidazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 58 (1.00 g, 5.0 mmol) and triethylamine (0.77 ml, 5.5 mmol) in anhydrous dichloromethane (10 ml) was added dropwise isobutyl chloroformate (2.60 ml, 20 mmol). The reaction mixture was stirred at room temperature for 18 h and then concentrated in vacuo. The residue was partitioned between water (10 ml) and ethyl acetate (10 ml) and the two layers were separated. The aqueous layer was extracted with ethyl acetate (10 ml) and the combined organic layers were dried (MgSO4) and concentrated in vacuo.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water (10 ml) and ethyl acetate (10 ml)
  3. customthe two layers were separated
  4. extractionThe aqueous layer was extracted with ethyl acetate (10 ml)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2421d87c1c447be8667d8a95f349e1f
Source dataset
uspto-grants-2009_09
Patent number
US07592362B2

Reaction notes

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