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

HRID 1445421
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HRID 1445421 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-0a9b4f48876b4fc483fe907417eba76f
출처 데이터셋
uspto-grants-2010_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07666834B2

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