Imidazole → HCID 58282634, compound

HRID 926002Notes

Reaction equation

HRID 926002 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][C@@H:8]([OH:11])[CH2:7][C@H:6]1[C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])=[O:4].[CH3:22][C:23]([Si:26](Cl)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)([CH3:25])[CH3:24].N1C=CN=C1>CN(C=O)C.C(Cl)Cl>[Si:26]([O:11][C@@H:8]1[CH2:9][CH2:10][C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[C@H:6]([C:12]([O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:13])[CH2:7]1)([C:23]([CH3:25])([CH3:24])[CH3:22])([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 58282620HCID 58282620, compound

Product 1

HCID 58282634HCID 58282634, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of compound 34d (10.9 mmol) in DMF (35 mL) were added TBDPSCl (24.0 mmol) and imidazole (32.7 mmol). The reaction mixture was stirred at room temperature for 16 hrs. The reaction mixture was then diluted with DCM (140 mL) and washed sequentially with 1N HCl (140 mL) and H2O (140 mL). Organics were dried, concentrated, and purified by silica gel chromatography (PE/EtOAc) to yield compound 35 as a colourless oil in 65% yield.

Workup

  1. washwashed sequentially with 1N HCl (140 mL) and H2O (140 mL)
  2. customOrganics were dried
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (PE/EtOAc)

Sources & evidence

ORD record
ord-87422dae9cec4ae480debfd5adc2419e
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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