Imidazole → (S)-Benzyl 3-[tert-butyldimethylsilyloxy]glutaramate

HRID 921495ノート

反応式

HRID 921495 の反応式
[CH2:1]([O:8][C:9](=[O:17])[CH2:10][C@@H:11]([OH:16])[CH2:12][C:13]([NH2:15])=[O:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:17])[CH2:10][C@@H:11]([O:16][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])[CH2:12][C:13]([NH2:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 89601064(S)-Benzyl-3-hydroxyglutaramate

生成物 1

HCID 125499654(S)-Benzyl 3-[tert-butyldimethylsilyloxy]glutaramate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
5 °C

実験手順

(S)-Benzyl-3-hydroxyglutaramate (100 g) was dissolved in dimethyl formamide. To this Imidazole (35 g) was added and the solution was cooled to 5° C. To this a solution of tert-butyldimethylsilylchloride (68.5 g) dissolved in dimethyl formamide (250 ml) was added under cooling. The mixture was warmed to 20-25° C. and stirred. The reaction mixture was cooled and quenched with water. To the reaction mixture ethyl acetate and water was added and stirred. The layers were separated and the organic phase was washed thrice with water. The organic phase was evaporated under reduced pressure to yield (S)-benzyl-3-(tert-butyl dimethylsilyloxy)glutaramate as oil.

後処理

  1. additionwas added
  2. temperatureunder cooling
  3. temperatureThe mixture was warmed to 20-25° C.
  4. temperatureThe reaction mixture was cooled
  5. customquenched with water
  6. additionTo the reaction mixture ethyl acetate and water was added
  7. stirringstirred
  8. customThe layers were separated
  9. washthe organic phase was washed thrice with water
  10. customThe organic phase was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-2c28ce0d3abe4c76b8897459480dc206
出典データセット
uspto-grants-2016_03
特許番号
US09273333B2

反応ノート

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