Imidazole → HCID 11761839, compound

HRID 1531574Notes

Reaction equation

HRID 1531574 reaction equation
[O:1]([CH3:13])[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].N1C=CN=C1.[C:19]([Si:23](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:22])([CH3:21])[CH3:20]>CN(C=O)C>[Si:23]([O:12][CH2:11][C@H:9]1[O:10][C@@H:2]([O:1][CH3:13])[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])([C:19]([CH3:22])([CH3:21])[CH3:20])([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 445238Methyl beta-D-glucopyranoside

Product 1

HCID 11761839HCID 11761839, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of methyl β-D-glucopyranoside (5 g, 25.7 mmol) in 51 mL of dry DMF was added at room temperature imidazole (5.46 g, 80.2 mmol) followed by tert-butyldiphenyl-silyl chloride (11.3 mL, 43.4 mmol). The solution was heated to 50° C. for 24 hours and the DMF was removed under reduced pressure. The reaction mixture was diluted with 200 mL of ethyl acetate and washed with H2O (1×100 mL), saturated aqueous NaCl (1×100 mL), and dried over magnesium sulfate. Concentration and flash chromatography (silica, 4% methanol in dichloromethane) provided pure target compound (9.82 g, 88%) as a white foam.

Workup

  1. customthe DMF was removed under reduced pressure
  2. additionThe reaction mixture was diluted with 200 mL of ethyl acetate
  3. washwashed with H2O (1×100 mL), saturated aqueous NaCl (1×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationConcentration and flash chromatography (silica, 4% methanol in dichloromethane)

Sources & evidence

ORD record
ord-5a941a9b92cb467291b376c7d8a14468
Source dataset
uspto-grants-2001_03
Patent number
US06197963B1

Reaction notes

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