Imidazole → HCID 86718375, compound

HRID 1518764Notes

Reaction equation

HRID 1518764 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C@@H:6]([N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:7]([CH3:11])[CH2:8][CH2:9][OH:10].N1C=CN=C1.[CH3:26][C:27]([Si:30](Cl)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([CH3:29])[CH3:28]>CN(C=O)C.CCOC(C)=O>[Si:30]([O:10][CH2:9][CH2:8][C@@H:7]([CH3:11])[C@H:6]([N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])[C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)([C:27]([CH3:29])([CH3:28])[CH3:26])([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 86718376HCID 86718376, compound

Product 1

HCID 86718375HCID 86718375, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2.18.1d (1.87 g, 6.60 mmol) in DMF (9.7 mL) at 0° C. was added imidazole (988 mg, 14.52 mmol, 2.2 equiv) and TBDPSCl (2.18 g, 7.92 mmol, 1.2 equiv). After stirring at room temperature for 12 hours, the reaction mixture was diluted with EtOAc (20 mL) and washed sequentially with water (5 mL), aqueous 1.0 M HCl solution, saturated aqueous NaHCO3 solution and brine. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (EtOAc/heptane) to give product 2.18.1e (3.55 g, yield 100%).

Workup

  1. washwashed sequentially with water (5 mL), aqueous 1.0 M HCl solution, saturated aqueous NaHCO3 solution and brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (EtOAc/heptane)
  5. customto give product 2.18.1e (3.55 g, yield 100%)

Sources & evidence

ORD record
ord-f5442b481a9d4bfe89f9ff9e1d35453b
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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