Imidazole → HCID 21705109, compound

HRID 1435953Notes

Reaction equation

HRID 1435953 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:14][OH:15])[CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:21](Cl)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>CN(C=O)C.C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:14][O:15][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:10][C:11]([OH:13])=[O:12])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 4323057HCID 4323057, compound

Product 1

HCID 21705109HCID 21705109, compound

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of 1 g of DL-3-tert-butoxycarbonylamino-4-hydroxy-butyric acid in a mixture of DMF/DCM 1:5, 1.24 g of imidazole and 1.7 g of tert-butyldimethylsilyl chloride were added. The solution was left stirring at room temperature overnight. The solution was extracted three times with 5% aq. NaHSO4 and the aqueous phases were washed twice with DCM. The organic extracts were dried over anh. sodium sulfate and the solvent evaporated under vacuum to provide 2.1 g of the title compound.

Workup

  1. additionwere added
  2. waitThe solution was left
  3. extractionThe solution was extracted three times with 5% aq. NaHSO4
  4. washthe aqueous phases were washed twice with DCM
  5. dry with materialThe organic extracts were dried over anh. sodium sulfate
  6. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-ea4b3dcf01ee4b39b41ddfa71adbab9e
Source dataset
uspto-grants-2009_11
Patent number
US07618982B2

Reaction notes

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