Benzyl Bromide → HCID 13967208, compound

HRID 1186020Notes

Reaction equation

HRID 1186020 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH:13]([OH:15])[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C.O>[CH2:23]([O:11][C:10](=[O:12])[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH:13]([OH:15])[CH3:14])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 100116N-(tert-butyloxycarbonyl)-L-threonine

Product 1

HCID 13967208HCID 13967208, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-3-hydroxybutanoic acid (3.0 g, 13.69 mmol) in DMF (50 mL) was added K2CO3 (3.73 g, 27.39 mmol) and stirred at RT for 15 min. (Bromomethyl)benzene (2.81 g, 16.43 mmol) was added and stirred at RT for 6 h. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (2×50 mL). The combined organic layer was washed with brine (50 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by silica gel column chromatography using 20% EtOAc/hexane as eluent to afford benzyl 2-(tert-butoxycarbonylamino)-3-hydroxybutanoate 10 (2.8 g, 66%).

Workup

  1. additionwas added
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic layer was washed with brine (50 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-746ceb22099c46139695f13ea6e36c7f
Source dataset
uspto-grants-2014_03
Patent number
US08673843B2

Reaction notes

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