Imidazole → HCID 14629888, compound

HRID 495603Notes

Reaction equation

HRID 495603 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][OH:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>CN(C=O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][O:17][Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 5314177Cbz-D-prolinol

Product 1

HCID 14629888HCID 14629888, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of D1 (9.70 g, 0.04 mol), imidazole (1.05 eq., 2.95 g) and tert-butyldimethylsilyl chloride (1.1 eq., 6.22 g) in DMF (dry, 50 ml) was stirred overnight at ambient temperature. Solvent was removed under reduced pressure and the residue partitioned between Et2O and water. The aqueous phase was separated and the organic phase washed with dilute HCl (0.5M, 2×100 ml), followed by water (2×100 ml) and the organic phase was then dried (anhydrous MgSO4), filtered and concentrated under reduced pressure to afford an oil (12.70 g). This was used in the next step without purification.

Workup

  1. customSolvent was removed under reduced pressure
  2. customthe residue partitioned between Et2O and water
  3. customThe aqueous phase was separated
  4. washthe organic phase washed with dilute HCl (0.5M, 2×100 ml)
  5. dry with materialthe organic phase was then dried (anhydrous MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f50dd52f6f494823b6494a092f53e6b3
Source dataset
uspto-grants-2005_09
Patent number
US06939891B2

Reaction notes

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