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Imidazole → 1-{[4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester

HRID 1445421
ノート
印刷プレビュー

反応式

HRID 1445421 の反応式
[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([OH:19])[CH2:16][NH:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2].N1C=CN=C1.[CH3:25][C:26]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])[CH3:27]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([NH:11][C:12]([CH:14]2[CH2:18][CH:17]([O:19][Si:29]([C:26]([CH3:28])([CH3:27])[CH3:25])([CH3:31])[CH3:30])[CH2:16][NH:15]2)=[O:13])[CH2:8][CH:7]1[CH:9]=[CH2:10])=[O:5])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 668712681-[(4-Hydroxy-pyrrolidine-2-carbonyl)-amino]-2-vinyl-cyclopropanecarboxylic acid ethyl ester

生成物 1

HCID 686756681-{[4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidine-2-carbonyl]-amino}-2-vinyl-cyclopropanecarboxylic acid ethyl ester収率 56%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

Compound 123 (6.5 g) and imidazole (3.4 g, 50 mmol) was dissolved in DCM (100 ml), TBDMSCl (3.9 g, 26 mmol) was added and the reaction mixture was left stirring at room temperature overnight. The reaction mixture was washed with aqueous citric acid and brine, dried over MgSO4 and evaporated. The crude product was purified by column chromatography on silica (EtOAc/n-Heptane 50/50-100/0) to give the title compound (4.26 g, 56%).

後処理

  1. waitthe reaction mixture was left
  2. washThe reaction mixture was washed with aqueous citric acid and brine
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customThe crude product was purified by column chromatography on silica (EtOAc/n-Heptane 50/50-100/0)

出典と根拠

ORDレコード
ord-0a9b4f48876b4fc483fe907417eba76f
出典データセット
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07666834B2

反応ノート

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