Water → 2-[4-({[2-(Acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)phenyl]ethyl tert-butyl hydrazine-1,2-dicarboxylate

HRID 1892491ノート

反応式

HRID 1892491 の反応式
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([C:10]([OH:12])=O)[N:9]=1)(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH:25]([C:34]([O:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([NH2:45])=[CH:41][CH:40]=1)=[O:35])[NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28].O>CN(C)C=O.C(OCC)(=O)C>[NH:25]([C:34]([O:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([NH:45][C:10]([C:8]2[N:9]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[S:6][CH:7]=2)=[O:12])=[CH:41][CH:40]=1)=[O:35])[NH:26][C:27]([O:29][C:30]([CH3:32])([CH3:33])[CH3:31])=[O:28]

参加物

7

反応物 4

HCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 8401132-Acetamido-1,3-thiazole-4-carboxylic acidHCID 581121152-(4-Aminophenyl)ethyl tert-butyl hydrazine-1,2-dicarboxylate

生成物 1

HCID 866500002-[4-({[2-(Acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)phenyl]ethyl tert-butyl hydrazine-1,2-dicarboxylate収率 79.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a suspension of 2-(acetylamino)-1,3-thiazole-4-carboxylic acid (557.3 mg, 2.993 mmol) in anhydrous N,N-dimethylformamide (10 ml) was added 1,1′-carbonyldiimidazole (531.7 mg, 3.279 mmol), and the mixture was stirred at 50° C. for 2 hr. 2-(4-Aminophenyl)ethyl tert-butyl hydrazine-1,2-dicarboxylate (1.065 g, 3.607 mmol) was added, and the mixture was stirred at room temperature for 16 hr. Water (100 ml) and ethyl acetate (100 ml) were added to the reaction mixture, and the mixture was stirred, stood still and partitioned. The organic layer was washed with 0.5M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was suspended in tert-butyl methyl ether (30 ml), filtered, washed 3 times with tert-butyl methyl ether, and dried under reduced pressure to give 2-[(4-({[2-(acetylamino)-1,3-thiazol-4-yl]carbonyl}amino)phenyl]ethyl tert-butyl hydrazine-1,2-dicarboxylate (1.098 g, 2.368 mmol, yield 79.1%) as a white solid.

後処理

  1. stirringthe mixture was stirred at room temperature for 16 hr
  2. stirringthe mixture was stirred
  3. custompartitioned
  4. washThe organic layer was washed with 0.5M hydrochloric acid, saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationfiltered
  8. washwashed 3 times with tert-butyl methyl ether
  9. customdried under reduced pressure

出典と根拠

ORDレコード
ord-59a81c8c26df4cc88438ca8daedfb48d
出典データセット
uspto-grants-2013_08
特許番号
US08507690B2

反応ノート

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