Imidazole → N-[3-acetylamino-2-(tert-butyldimethylsilanyloxy) propyl]acetamide

HRID 76239ノート

反応式

HRID 76239 の反応式
[C:1]([NH:4][CH2:5][CH:6]([OH:12])[CH2:7][NH:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].N1C=CN=C1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].O.CCOCC>CN(C=O)C>[C:9]([NH:8][CH2:7][CH:6]([O:12][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23])[CH2:5][NH:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

参加物

6

反応物 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 332254HCID 332254、化合物HCID 21584184Diethylether water

生成物 1

HCID 86698889N-[3-acetylamino-2-(tert-butyldimethylsilanyloxy) propyl]acetamide収率 93%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of N-(3-acetylamino-2-hydroxypropyl)acetamide (synthesized as described in J. Org. Chem., 2000, 65(4), 1200, which is incorporated herein by reference in its entirety) (741 mg, 4.25 mmol) and 1H-imidazole (579 mg, 8.51 mmol) in dry DMF (17 mL), a solution of tert-butylchlorodimethylsilane (962 mg, 6.38 mmol) in dry DMF (8 mL) was added dropwise, and the reaction was stirred at r.t. overnight. The reaction was portioned between H2O/Et2O, the phases were separated and the aqueous layer was washed twice with Et2O and three times with EtOAc. All the organics were combined, dried over Na2SO4, filtered and concentrated, affording N-[3-acetylamino-2-(tert-butyldimethylsilanyloxy) propyl]acetamide (1140 mg, 3.95 mmol, 93% yield) as off-white solid.

後処理

  1. customthe phases were separated
  2. washthe aqueous layer was washed twice with Et2O and three times with EtOAc
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-517a872a26be4324b062ae8078ef9fc6
出典データセット
uspto-grants-2014_09
特許番号
US08835494B2

反応ノート

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