Imidazole → HCID 131720786, compound

HRID 481728Notes

Reaction equation

HRID 481728 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1([O:11][C@H:10]([CH2:12][O:13][C:14](=[O:21])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9][C@H:7]1[OH:8])[OH:6].N1C=CN=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:1][O:2][CH2:3][CH2:4][C:5]1([O:11][C@H:10]([CH2:12][O:13][C:14](=[O:21])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:9][C@H:7]1[O:8][Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28])[OH:6]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 516892Sodium BicarbonateHCID 131720787HCID 131720787, compound

Product 1

HCID 131720786HCID 131720786, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2-methoxyethyl)-5-O-benzoyl-3-deoxy-D-xylofuranose (example 122) (9.59 g, 32.40 mmol) and imidazole (3.980 g, 58.47 mmol) in DMF (40 mL ) at room temperature was added t-butyldimethylsilyl chloride (6.35 g, 42.12 mmol). The solution was stirred for 3 h and saturated NaHCO3 was added. The mixture was concentrated under vacuo. The residue was then partitioned between ether (100 mL) and water (50 mL). The aqueous phase was further extracted with ether (2×50 mL). The combined extracts were washed with brine (2×50 mL) dried (MgSO4) and concentrated to give the title compound (13.3 g, 100%)

Workup

  1. concentrationThe mixture was concentrated under vacuo
  2. customThe residue was then partitioned between ether (100 mL) and water (50 mL)
  3. extractionThe aqueous phase was further extracted with ether (2×50 mL)
  4. washThe combined extracts were washed with brine (2×50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4ee745076ab74488a925e954aa59ee64
Source dataset
uspto-grants-1998_08
Patent number
US05789394

Reaction notes

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