Citric Acid → tert-Butyl 3-[4-[(benzyloxy)methyl]-2-{[4-(trifluoromethoxy)phenyl]-imino}thiazol-3(2H)-yl]propylcarbamate

HRID 747508Notes

Reaction equation

HRID 747508 reaction equation
[OH:1][CH2:2][C:3]1[N:4]([CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:5](=[N:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:18])[F:17])=[CH:11][CH:10]=2)[S:6][CH:7]=1.[H-].[Na+].[CH2:33](Br)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C=O>[CH2:33]([O:1][CH2:2][C:3]1[N:4]([CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[C:5](=[N:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([F:19])([F:17])[F:18])=[CH:11][CH:10]=2)[S:6][CH:7]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 22351040tert-Butyl 3-[4-(hydroxymethyl)-2-{[4-(trifluoromethoxy)phenyl]-imino}thiazol-3(2H)-yl]propylcarbamate

Product 1

HCID 22350977tert-Butyl 3-[4-[(benzyloxy)methyl]-2-{[4-(trifluoromethoxy)phenyl]-imino}thiazol-3(2H)-yl]propylcarbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound (313 mg) obtained in the above (2) was dissolved in N,N-dimethylformamide (3 ml), and thereto was added sodium hydride (56 mg, 60% dispersion in oil) in an ice bath under nitrogen atmosphere, and the mixture was stirred for 30 minutes. To the reaction mixture was added benzyl bromide (179 mg), and the mixture was warmed to room temperature, and then stirred for one hour. The reaction mixture was poured into a 10% aqueous citric acid solution under ice-cooling, and the mixture was extracted with chloroform. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (5:1)] to give the title compound (137 mg) as oil.

Workup

  1. stirringstirred for one hour
  2. temperaturecooling
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with a saturated brine
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (5:1)]

Sources & evidence

ORD record
ord-cfc653a21b4642eaa95e5f8a27acbb0b
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

Loading…