Benzyl Bromide → Boc-Azidoalanine benzyl ester

HRID 575917Notes

Reaction equation

HRID 575917 reaction equation
[C:1]([N:8]([N:14]=[N+:15]=[N-:16])[C@H:9]([C:11]([OH:13])=[O:12])[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C>C(#N)C.C(OCC)(=O)C.CCCCCC>[CH2:17]([O:12][C:11](=[O:13])[C@H:9]([CH3:10])[N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2])[N:14]=[N+:15]=[N-:16])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 3036707N-tert-Butyloxycarbonyl-dl-azidoalanine

Product 1

HCID 68279958Boc-Azidoalanine benzyl esterYield 63%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Boc-azidoalanine 8 (520 mg, 2.26 mmol) was dissolved in dry acetonitrile (8 mL) in glass vial equipped with a magnetic stir bar and capped with a septum. Benzyl bromide (325 μL, 2.71 mmol) and diisopropylethylamine (440 μL, 2.49 mmol) were subsequently added via syringe. The solution was stirred for 18 h at room temperature until TLC indicated the consumption of the starting material. The reaction mixture was concentrated in vacuo and the crude product was loaded onto a silica gel column. The column was eluted first with 10% ethyl acetate/hexane to wash off the residual benzyl bromide and then with 20% ethyl acetate/hexane to elute the product (452 mg, 63% yield).

Workup

  1. customvial equipped with a magnetic stir bar
  2. customcapped with a septum
  3. customthe consumption of the starting material
  4. concentrationThe reaction mixture was concentrated in vacuo
  5. washThe column was eluted first with 10% ethyl acetate/hexane
  6. washto wash off the residual benzyl bromide

Sources & evidence

ORD record
ord-1380b9fdb8dc4878930ed9e4187cd3e5
Source dataset
uspto-grants-2015_05
Patent number
US09035068B2

Reaction notes

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