Imidazole → t-Butyldimethylsilyloxyserine methyl ester

HRID 1734684ノート

反応式

HRID 1734684 の反応式
Cl.[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH2:6].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].CN(C=[O:27])C>CCOCC>[CH3:2][O:3][C:4](=[O:9])[C@H:5]([CH2:7][OH:8])[NH:6][O:27][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

参加物

6

反応物 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

生成物 1

HCID 22856314t-Butyldimethylsilyloxyserine methyl ester

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
25 °C

実験手順

Serine methyl ester hydrochloride [HOCH2CH(NH2)CO2CH3. HCl] (18.7 g; 0.120 mol) and imidazole (30 g; 0.44 mol) are dissolved in DMF (100 ml) and cooled to 0° C. t-Butyldimethylsilyl chloride (19.5 g; 0.13 mol) is added and the reaction allowed to stir 15 hours at 25° C. The reaction is then diluted with ether (2 L), washed with water (4x 500 ml), dried (MgSO4) and concentrated to yield t-butyldimethylsilyloxyserine methyl ester as an oil which is used directly in Step B.

後処理

  1. additionis added
  2. washwashed with water (4x 500 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-e6de6bce13894bee8a8e60dfb2cbcae9
出典データセット
uspto-grants-1996_07
特許番号
US05534532

反応ノート

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