Imidazole → HCID 131720786, compound

HRID 365788Notes

Reaction equation

HRID 365788 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 wasadded. 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-68e532c6405240b9a868d9bda8c666a4
Source dataset
uspto-grants-2000_10
Patent number
US06127540

Reaction notes

Loading…