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1,1'-Carbonyldiimidazole → N-[[3,5-bis-(trifluoromethyl)phenyl]methyl]-3,4-dichloro-beta-(2-hydroxyethyl)-N-methyl-benzenepropanamide

HRID 2256322
ノート
印刷プレビュー

反応式

HRID 2256322 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:14][C:15]([N:17]([CH2:19][C:20]2[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[C:22]([C:30]([F:33])([F:32])[F:31])[CH:21]=2)[CH3:18])=[O:16])[CH2:10][C:11](O)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N1C=CN=C1)(N1C=CN=C1)=O.[BH4-].[Na+]>CCOC(C)=O.O>[F:33][C:30]([F:31])([F:32])[C:22]1[CH:21]=[C:20]([CH2:19][N:17]([CH3:18])[C:15](=[O:16])[CH2:14][CH:9]([CH2:10][CH2:11][OH:12])[C:4]2[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=2)[CH:25]=[C:24]([C:26]([F:28])([F:29])[F:27])[CH:23]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4311764Sodium borohydrideHCID 19029324HCID 19029324、化合物

生成物 1

HCID 19029400N-[[3,5-bis-(trifluoromethyl)phenyl]methyl]-3,4-dichloro-beta-(2-hydroxyethyl)-N-methyl-benzenepropanamide収率 96%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 8857
Ethyl Acetate
溶媒
2 回

実験手順

3,4-Dichloro-β[2-[[3,5-bis-(trifluoromethyl)phenylmethyl]methylamino]-2-oxoethyl]-benzenepropanoic acid (6.1 g) in EtOAc (75 mL) was treated with carbonyldiimidazole (2.43 g) and N,N-dimethylaminopyridine (150 mg). The resulting solution was stirred at room temperature for 15 minutes and then heated at 50° C. for two hours. The reaction mixture was cooled to 0° C. and treated with a solution of NaBH4 (1.8 g) in H2O (30 mL), warmed slowly to room temperature and stirred for 12 hours. The reaction mixture was diluted with EtOAc (150 mL) and washed with 1N HCl (1×100 mL), sat. NaHCO3 (1×100 mL) and water (1×100 mL). The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure to yield the crude compound as a oil. Silica gel chromatography eluting with 0-10% MeOH/CH2Cl2 gave the title compound (5.7 g). Mass spectrum (FAB): 502.0791.

後処理

  1. temperatureheated at 50° C. for two hours
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. temperaturewarmed slowly to room temperature
  4. stirringstirred for 12 hours
  5. washwashed with 1N HCl (1×100 mL), sat. NaHCO3 (1×100 mL) and water (1×100 mL)
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield the crude compound as a oil
  10. washSilica gel chromatography eluting with 0-10% MeOH/CH2Cl2

出典と根拠

ORDレコード
ord-b057f8a790764a6d8fa590917b14d426
出典データセット
uspto-grants-1997_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05654316

反応ノート

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