Benzyl Bromide → HCID 69609857, compound

HRID 1245125Notes

Reaction equation

HRID 1245125 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH:4]([NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5][OH:6].[H-].[Na+].[H][H].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH3:1][O:2][C:3](=[O:15])[C@@H:4]([NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:5][O:6][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 495564Methyl N-(tert-butoxycarbonyl)serinateHCID 178418361HCID 178418361, compound

Product 1

HCID 69609857HCID 69609857, compoundYield 120%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-tert-Butoxycarbonylamino-3-hydroxy-propionic acid methyl ester (0.400 g, 1.82 mmol) in dimethylformamide (15 ml) was added sodium hydride (65%)(0.145 g, 3.64 mmol) at 0° C. after the evolution of hydrogen gas ceased, the freshly distilled benzyl bromide (0.449 g, 1.82 mmol) was added to the solution. The reaction mixture was stirred at 25–30° C. for 5 hr to give a clear solution The solvent was then removed under reduced pressure below 40° C. The residue was dissolved in water (30 ml) and the solution extracted with ethyl acetate (two 20 ml portions). The combined organic layers were further washed with brine and dried over anhydrous sodium sulfate. The ethyl acetate was then removed under reduced pressure to give the 3-(biphenyl-4-ylmethoxy)-(2S)-tert-butoxycarbonylamino-propionic acid methyl ester as colorless oil (0.421 g, 60%). LC/MS (m/z): 386(M+1).

Workup

  1. customto give a clear solution The solvent
  2. customwas then removed under reduced pressure below 40° C
  3. dissolutionThe residue was dissolved in water (30 ml)
  4. extractionthe solution extracted with ethyl acetate (two 20 ml portions)
  5. washThe combined organic layers were further washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe ethyl acetate was then removed under reduced pressure

Sources & evidence

ORD record
ord-b25bca12d4254ba3855e8ac86cf52d2a
Source dataset
uspto-grants-2006_10
Patent number
US07122580B2

Reaction notes

Loading…