Imidazole → HCID 57260263, compound

HRID 1626303Notes

Reaction equation

HRID 1626303 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.N1C=CN=C1.[CH3:21][C:22]([Si:25](Cl)([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C=O)C>[Si:25]([O:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:22]([CH3:24])([CH3:23])[CH3:21])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 562256Benzyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 57260263HCID 57260263, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Benzyl 3-hydroxypropylcarbamate obtained in step 1 (15 g, 72 mmol) was treated with imidazole (10 g, 146.9 mmol) and TBSCl (12 g, 79.6 mmol) in DMF (10 ml) at 0° C. After warming up the resulting reaction mixture to room temperature, it was stirred for 30 minutes. The resulting solution was quenched with water (50 ml), and then extracted with diethyl ether twice (50 ml×2). After evaporation of volatile material under reduced pressure, the residue was purified with silica gel column chromatography (EtOAc:Hx=1:10) to afford the title compound (23 g, 98%) as colorless oil.

Workup

  1. temperatureAfter warming up
  2. customthe resulting reaction mixture to room temperature
  3. customThe resulting solution was quenched with water (50 ml)
  4. extractionextracted with diethyl ether twice (50 ml×2)
  5. customAfter evaporation of volatile material under reduced pressure
  6. customthe residue was purified with silica gel column chromatography (EtOAc:Hx=1:10)

Sources & evidence

ORD record
ord-b6ebaee31d0945baba0749214332a87f
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Reaction notes

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