Imidazole → HCID 86718383, compound

HRID 1518770Notes

Reaction equation

HRID 1518770 reaction equation
[CH3:1][C:2]([Si:5](Cl)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:4])[CH3:3].N1C=CN=C1.[OH:24][C@H:25]([CH2:46][OH:47])[C@H:26]([NH:35][C:36](=[O:45])[O:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1>CN(C=O)C.CCOC(C)=O>[Si:5]([O:47][CH2:46][C@@H:25]([OH:24])[C@H:26]([NH:35][C:36](=[O:45])[O:37][CH2:38][C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=1)([C:2]([CH3:4])([CH3:3])[CH3:1])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 86718381HCID 86718381, compound

Product 1

HCID 86718383HCID 86718383, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

TBDPSCl (3.5 g, 12.6 mmol, 1.1 equiv) and imidazole (1.95 g, 28.7 mmol, 2.5 equiv) were added to a solution of 2.21.1b (3.8 g, 11.4 mmol, 1.0 equiv) in DMF (11.5 mL) at room temperature and the mixture was stirred at room temperature for 1 hour. The mixture was diluted with EtOAc and washed with saturated aqueous NH4Cl solution, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel column chromatography (EtOAc/heptane, 0 to 50%) to give product 5.4 g (83% yield). MS m/z (M+Na) 592

Workup

  1. washwashed with saturated aqueous NH4Cl solution, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (EtOAc/heptane, 0 to 50%)

Sources & evidence

ORD record
ord-b21f5e872e354e66b4e7f4ded2a63355
Source dataset
uspto-grants-2015_07
Patent number
US09072696B2

Reaction notes

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