Imidazole → HCID 86591802, compound

HRID 896897Notes

Reaction equation

HRID 896897 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[N:13]=[CH:12][C:11]([C@@H:14]([OH:36])[CH2:15][N:16]([CH2:24][C@H:25]3[CH2:34][CH2:33][C:32]4[C:27](=[CH:28][CH:29]=[C:30]([I:35])[CH:31]=4)[O:26]3)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:10][CH:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[CH3:37][C:38]([Si:41](Cl)([CH3:43])[CH3:42])([CH3:40])[CH3:39].N1C=CN=C1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Si:41]([O:36][C@H:14]([C:11]1[CH:12]=[N:13][C:8]([N:3]2[C:4]([CH3:7])=[CH:5][CH:6]=[C:2]2[CH3:1])=[CH:9][CH:10]=1)[CH2:15][N:16]([CH2:24][C@H:25]1[CH2:34][CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([I:35])[CH:31]=2)[O:26]1)[C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])([C:38]([CH3:40])([CH3:39])[CH3:37])([CH3:43])[CH3:42]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 59118180HCID 59118180, compound

Product 1

HCID 86591802HCID 86591802, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of tert-butyl (2R)-2-[6-(2,5-dimethyl-1H-pyrrol-1-yl)-3-pyridinyl]-2-hydroxyethyl{[(2R)-6-iodo-3,4-dihydro-2H-chromen-2-yl]methyl}carbamate (Example 357, 7.5 g, 12.4 mmol), TBDMSCl (2.25 g, 14.9 mmol), and imidazole (2.10 g, 30.9 mmol) in DMF (10 mL) was stirred at room temperature under argon for 24 hours. The reaction mixture was then poured into a saturated NaHCO3 solution (50 mL). The mixture was extracted with ether (100 mL×2). The ether layer was washed with water (50 mL) and dried over anhydrous sodium sulfate. Removal of the solvent in vacuo afforded a near white syrup which was purified by column chromatography (silica gel, hexanes/ethyl acetate (5/1, v/v)) and gave the desired compound as a colorless oil (6.5 g, 72%).

Workup

  1. extractionThe mixture was extracted with ether (100 mL×2)
  2. washThe ether layer was washed with water (50 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. customRemoval of the solvent in vacuo
  5. customafforded a near white syrup which
  6. customwas purified by column chromatography (silica gel, hexanes/ethyl acetate (5/1

Sources & evidence

ORD record
ord-5b87258cd7994bf6ac5c4f54af2c9124
Source dataset
uspto-grants-2005_07
Patent number
US06919371B2

Reaction notes

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