Imidazole → HCID 59518835, compound

HRID 1161780Notes

Reaction equation

HRID 1161780 reaction equation
[OH:1][CH:2]([CH2:15][OH:16])[CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH3:17][C:18]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])[CH3:19].N1C=CN=C1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.CO.CCOC(C)=O>[Si:21]([O:1][CH:2]([CH2:15][OH:16])[CH2:3][NH:4][C:5](=[O:14])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:18]([CH3:20])([CH3:19])[CH3:17])([CH3:23])[CH3:22]

Participants

8

Reactant 4

HCID 795ImidazoleHCID 6101p-Toluenesulfonic acidHCID 28928tert-Butyldimethylsilyl chlorideHCID 3362144N-(Benzyloxycarbonyl)-3-amino-1,2-propanediol

Product 1

HCID 59518835HCID 59518835, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of benzyl 2,3-dihydroxypropylcarbamate in DMF (0.1 M) was added TBDMSCl (2.2 eq.) and imidazole (2.5 eq.) at room temperature. After stirred for 20 h, the reaction mixture was worked up with EtOAc, which was washed with water and brine. The organic layer was separated, dried and concentrated to give the crude bis-silylated product, which was dissolved in methanol (0.16 M) followed by addition of p-toluenesulfonic acid (0.1 equiv.) at 0° C. The reaction mixture was stirred for 1.5 h at the same temperature. After quenched with saturated NaHCO3 aqueous solution, the reaction mixture was extracted with EtOAc, which was washed with water and brine. The organic layer was separated, dried, concentrated, and purified on silica gel with 0-100% EtOAc/Hexanes gradient elution to provide the pure benzyl 2-(tert-butyldimethylsilyloxy)-3-hydroxypropylcarbamate.

Workup

  1. washwas washed with water and brine
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated
  5. customto give the crude bis-silylated product, which
  6. stirringThe reaction mixture was stirred for 1.5 h at the same temperature
  7. customAfter quenched with saturated NaHCO3 aqueous solution
  8. extractionthe reaction mixture was extracted with EtOAc, which
  9. washwas washed with water and brine
  10. customThe organic layer was separated
  11. customdried
  12. concentrationconcentrated
  13. custompurified on silica gel with 0-100% EtOAc/Hexanes gradient elution

Sources & evidence

ORD record
ord-49c34ead2d654796aa40eca11fa8b9bb
Source dataset
uspto-grants-2010_10
Patent number
US07820646B2

Reaction notes

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