Imidazole → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-ylcarbamate

HRID 340896ノート

反応式

HRID 340896 の反応式
[OH:1][CH2:2][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][CH:5]=[CH2:6].N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[Si:20]([O:1][CH2:2][C@@H:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:4][CH:5]=[CH2:6])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 14153343Tert-butyl (s)-(1-hydroxypent-4-en-2-yl)carbamate

生成物 1

HCID 14153345(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-ylcarbamate収率 85.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-tert-butyl 1-hydroxypent-4-en-2-ylcarbamate (165 g, 0.82 mol) and imidazole (72.5 g, 1.07 mol) in DCM (3 L) was added TBS-Cl (135.4 g, 0.9 mol). The reaction was stirred at RT overnight and filtered. The filtrate was concentrates. The resulting residue was dissolved in EtOAc (L) and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated to give (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-ylcarbamate (222.0 g), which was used in the next step without further purification. LRMS (M+H+) m/z 316.2.

後処理

  1. filtrationfiltered
  2. dissolutionThe resulting residue was dissolved in EtOAc (L)
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-9f7a37b26f0247edbca55dd8862db73c
出典データセット
uspto-grants-2014_11
特許番号
US08895582B2

反応ノート

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