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

HRID 1445421Notes

Reaction equation

HRID 1445421 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-0a9b4f48876b4fc483fe907417eba76f
Source dataset
uspto-grants-2010_02
Patent number
US07666834B2

Reaction notes

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