Imidazole → Benzyl 3-(2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)phenylcarbamate

HRID 221405Notes

Reaction equation

HRID 221405 reaction equation
[OH:1][CH:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]=[CH:9][CH:10]=1)[CH2:3][OH:4].N1C=CN=C1.[CH3:27][C:28]([Si:31](Cl)([CH3:33])[CH3:32])([CH3:30])[CH3:29]>CN(C=O)C>[Si:31]([O:4][CH2:3][CH:2]([C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:8]=[CH:9][CH:10]=1)[OH:1])([C:28]([CH3:30])([CH3:29])[CH3:27])([CH3:33])[CH3:32]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 67328809benzyl N-[3-(1,2-dihydroxyethyl)phenyl]carbamate

Product 1

HCID 67329796Benzyl 3-(2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)phenylcarbamateYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Benzyl 3-(1,2-dihydroxyethyl)phenylcarbamate (8 g) was dissolved in dry DMF (50 mL) and cooled to 0° C. Imidazole (2.8 g) and TBSCl (5 g) were added and the mixture was stirred at room temperature for 24 hours. The reaction was quenched by addition of water (100 mL) and extracted with EtOAc (2×100 mL). The organic phase was separated, dried over Na2SO4 and concentrated to give a crude product which was purified by column chromatography to give the title compound (6 g, 60%).

Workup

  1. customThe reaction was quenched by addition of water (100 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a crude product which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-05fd61c287894b6580c56192e67ce4a2
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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