Imidazole → HCID 21710118, compound

HRID 650919Notes

Reaction equation

HRID 650919 reaction equation
[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH2:15][OH:16])=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19].N1C=CN=C1>CN(C=O)C>[OH:1][C:2]1[C:14]2[C:13]3[C:8](=[CH:9][C:10]([CH2:15][O:16][Si:22]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:25])[CH3:24])=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 21706143HCID 21706143, compound

Product 1

HCID 21710118HCID 21710118, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 332.2 mg (1.47 mmol) of the diol from Step H, 243.5 mg (1.61 mmol) of t-butyldimethylchlorosilane, and 120 mg (1.76 mmol) of imidazole in 8 mL of sieve dried DMF was stirred at 100° C. for 45 minutes. The mixture was partitioned between EtOAc, ice-water and 2N HCl, and the organic phase was separated, washed twice with ice-water, and then with brine, dried over Na2SO4, filtered, evaporated, and dried in vacuo. Purification by PLC using CH2Cl2-EtOAc (50:1) gave 447.4 mg of the title material.

Workup

  1. customThe mixture was partitioned between EtOAc, ice-water and 2N HCl
  2. customthe organic phase was separated
  3. washwashed twice with ice-water
  4. dry with materialwith brine, dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customdried in vacuo
  8. customPurification by PLC

Sources & evidence

ORD record
ord-9d7e7067afb741eab7fbda2627605397
Source dataset
uspto-grants-2001_08
Patent number
US06277843B1

Reaction notes

Loading…