Imidazole → HCID 59614329, compound

HRID 409470Notes

Reaction equation

HRID 409470 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]([CH2:14][CH3:15])[CH2:9][C@H:10]([OH:13])[CH:11]=[CH2:12])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C=O)C>[C:1]([O:5][C:6](=[O:16])[NH:7][C@H:8]([CH2:14][CH3:15])[CH2:9][C@H:10]([O:13][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:11]=[CH2:12])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 15881262HCID 15881262, compound

Product 1

HCID 59614329HCID 59614329, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ((1R,3S)-1-ethyl-3-hydroxy-pent-4-enyl)-carbamic acid tert-butyl ester (0.541 mmol; 124 mg) and imidazole (2.164 mmol; 147 mg) in DMF (1.8 mL) is added tert-butyldimethylsilyl chloride (1.623 mmol; 245 mg) at room temperature under N2. After 12 hours, the reaction mixture is quenched with water, extracted three times with EtOAc. The combined organic layer is washed with brine, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc) to give [(1R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-1-ethyl-pent-4-enyl]-carbamic acid tert-butyl ester (160 mg, 86%); ESI-MS m/z: 288 [M+−tBu+2], Retention time 5.77 min (condition B).

Workup

  1. customthe reaction mixture is quenched with water
  2. extractionextracted three times with EtOAc
  3. washThe combined organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc)

Sources & evidence

ORD record
ord-c5914cdf4a3d4790b7153dbaed83c2de
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

Loading…