Imidazole → HCID 70234588, compound

HRID 651546Notes

Reaction equation

HRID 651546 reaction equation
[NH2:1][C@H:2]1[C@@H:14]2[C:15](=[O:18])[O:16][CH2:17][C@H:13]2[C@H:12]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([OH:27])=[C:21]([O:28][CH3:29])[CH:20]=2)[C:11]2[C:3]1=[CH:4][C:5]1[O:9][CH2:8][O:7][C:6]=1[CH:10]=2.N1C=CN=C1.[Si:35](Cl)([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].O>CN(C)C=O.CCOCC>[NH2:1][C@H:2]1[C@@H:14]2[C:15](=[O:18])[O:16][CH2:17][C@H:13]2[C@H:12]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[C:22]([O:27][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])=[C:21]([O:28][CH3:29])[CH:20]=2)[C:11]2[C:3]1=[CH:4][C:5]1[O:9][CH2:8][O:7][C:6]=1[CH:10]=2

Participants

7

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 70236857HCID 70236857, compound

Product 1

HCID 70234588HCID 70234588, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 7.4 mmol of the compound of Example 14, 58.8 mmol of imidazole and 13 mmol of tert-butyldimethylsilyl chloride in 225 ml of anhydrous dimethylformarnide is stirred at ambient temperature. After reaction for 17 hours, the mixture is poured into a mixture of water and ether. After exraction with ether, the combined organic phases are dried, filtered and then concentrated under reduced pressure. The residue is subsequently recrystallised from a heptane/benzene mixture enabling the expected product to be isolated.

Workup

  1. customAfter reaction for 17 hours
  2. dry with materialAfter exraction with ether, the combined organic phases are dried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is subsequently recrystallised from a heptane/benzene mixture
  6. customto be isolated

Sources & evidence

ORD record
ord-ea8673a4c99044da9037241d357ce822
Source dataset
uspto-grants-2001_08
Patent number
US06281198B1

Reaction notes

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