Benzyl Bromide → Benzyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinate

HRID 1003715Notes

Reaction equation

HRID 1003715 reaction equation
[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:12]([OH:14])=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(OCC)(=O)C>[NH:1]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@H:2]([C:12]([O:14][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:13])[CH2:3][O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Product 1

HCID 13384475Benzyl O-benzyl-N-(tert-butoxycarbonyl)-L-serinateYield 70%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

BocSer(Bzl) 60 g (0.2 mol) was added to 400 ml of ethyl acetate, to which triethylamine 21 g (0.2 mol) and benzyl bromide 35.4 g (0.2 mol) were added and reacted under refluxing condition for 4 hours. After cooled, the salt produced was separated by filtration. The filtrate was washed with an aqueous NaHCO3 solution and an aqueous NaCl solution and then dried over Na2SO4 and concentrated to dryness to obtain 54 g of white powder (Yield: 68%).

Workup

  1. additionwere added
  2. customreacted
  3. temperatureunder refluxing condition for 4 hours
  4. temperatureAfter cooled
  5. customthe salt produced
  6. customwas separated by filtration
  7. washThe filtrate was washed with an aqueous NaHCO3 solution
  8. dry with materialan aqueous NaCl solution and then dried over Na2SO4
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-138791f61120403783737c9418916ff9
Source dataset
uspto-grants-2000_04
Patent number
US06046289

Reaction notes

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