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

HRID 747508ノート

反応式

HRID 747508 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)]

出典と根拠

ORDレコード
ord-cfc653a21b4642eaa95e5f8a27acbb0b
出典データセット
uspto-grants-2008_07
特許番号
US07396842B2

反応ノート

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