Allyl bromide → N-Boc-O-allyl-L-homoserine

HRID 627590Notes

Reaction equation

HRID 627590 reaction equation
[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][OH:5].[H-].[Na+].[CH2:18](Br)[CH:19]=[CH2:20]>CN(C=O)C>[NH:1]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C@H:2]([C:6]([OH:8])=[O:7])[CH2:3][CH2:4][O:5][CH2:20][CH:19]=[CH2:18]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 13066457(2S)-2-(((tert-butoxy)carbonyl)amino)-4-hydroxybutanoic acid

Product 1

HCID 58798660N-Boc-O-allyl-L-homoserineYield 67.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Boc-L-HomoSer-OH (10.0 g, 45.6 mmol) in DMF was added sodium hydride (2.74 g, 114 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 15 mins, and then allyl bromide (6.90 g, 57.0 mmol) was added. The mixture was warmed to 20° C. and stirred for 2 hrs. The mixture was quenched with saturated NH4Cl solution and then concentrated in vacuum. The residue was diluted with water, and sequentially washed with hexane and ether. The organic layers were discarded, and the aqueous layer was carefully adjusted to pH=3 with 1 N HCl. The acidic aqueous solution was extracted with ethyl acetate. The organic phase was dried over MgSO4 and concentrated in vacuum to give Boc-L-HomoSer(O-allyl)-OH (8.00 g, 67.8%).

Workup

  1. temperatureThe mixture was warmed to 20° C.
  2. stirringstirred for 2 hrs
  3. customThe mixture was quenched with saturated NH4Cl solution
  4. concentrationconcentrated in vacuum
  5. additionThe residue was diluted with water
  6. washsequentially washed with hexane and ether
  7. extractionThe acidic aqueous solution was extracted with ethyl acetate
  8. dry with materialThe organic phase was dried over MgSO4
  9. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-28edd477a31944629ed68478f3f40267
Source dataset
uspto-grants-2016_04
Patent number
US09309285B2

Reaction notes

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