Methyl iodide → HCID 22847664, compound

HRID 6477Notes

Reaction equation

HRID 6477 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15](=[O:43])[C@H:16]([CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[N:17]=[CH:18][C:19]1[N:23]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[C:22]([CH2:32][CH2:33][CH2:34][CH3:35])=[N:21][CH:20]=1.CI>O1CCCC1>[CH3:13][O:14][C:15](=[O:43])[C@:16]([CH3:1])([CH2:36][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[N:17]=[CH:18][C:19]1[N:23]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[C:22]([CH2:32][CH2:33][CH2:34][CH3:35])=[N:21][CH:20]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 53683259[{1-[(2-chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}methylene]phenylalanine methyl esterHCID 178418339Butyllithium

Product 1

HCID 22847664HCID 22847664, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a solution of diisopropylamine (1.27 g, 12.6 mmol) in tetrahydrofuran (50 ml) was added n-butyl lithium (5 ml of 2.5M in hexane, 12.6 mmol) at 0° C. After being stirred at 0° C. for 15 minutes, the solution was cooled to -78° C. and a solution of the imine, N [{1-[(2-chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}methylene]phenylalanine methyl ester (Example 3(i) Method B) (5.51 g, 12.6 mmol) in tetrahydrofuran (35 ml) was added dropwise. The mixture was stirred for 30 minutes at -78° C. under argon and methyl iodide (2.06 q, 14.5 mmol) in tetrahydrofuran (15 ml) was added at 78° C. The mixture was allowed to slowly warm to ambient temperature and then stirred for 18 hours. The solvent was evaporated, the residue dissolved in ethyl acetate, the insoluble materials were filtered and the concentrated product was used without purification to give 8N18 g of N-[{1-[(2-chlorophenyl)-methyl]-2-n-butyl-1H-imidazol-5-yl}methylene]-α-methylphenyl-alanine methyl ester.

Workup

  1. temperaturethe solution was cooled to -78° C.
  2. stirringThe mixture was stirred for 30 minutes at -78° C. under argon
  3. temperatureto slowly warm to ambient temperature
  4. stirringstirred for 18 hours
  5. customThe solvent was evaporated
  6. dissolutionthe residue dissolved in ethyl acetate
  7. filtrationthe insoluble materials were filtered
  8. customthe concentrated product was used without purification

Sources & evidence

ORD record
ord-e18ec41772ca4d5fa1f5d0902ef672de
Source dataset
uspto-grants-1993_09
Patent number
US05248689

Reaction notes

Loading…