Benzyl Bromide → HCID 178512913, compound

HRID 555024Notes

Reaction equation

HRID 555024 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].C([O-])([O-])=O.[Cs+].[Cs+].[Cs].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CO.O.CN(C=O)C>[NH2:1][C@H:2]([C:10]([O:12][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8]

Participants

8

Reactant 4

HCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 5354618CesiumHCID 178454187HCID 178454187, compound2×

Product 1

HCID 178512913HCID 178512913, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Water (2 ml) was added to a solution of Boc-Arg-OH (2.5 mmol) in methanol (20 ml). The solution was neutralised with a 20% solution of Cs2CO3 in water and then evaporated in vacuo to dryness. Residual water was removed by repeated addition and evaporation of toluene. The solid cesium salt of Boc-arginine was treated with DMF (25 ml) and benzyl bromide (3 mmol) and stirred at room temperature for 6 h. The DMF was removed in vacuo and the product was dissolved in acetone and filtered. The filtrate was evaporated in vacuo and the product was treated with 95% trifluoroactetic acid (TFA) (4 ml). The resulting product H-Arg-OBzl was isolated by tituration by diethyl ether. The salt of H-Arg-OBzl was isolated by treating the product with para-toluenesulfonic acid (5 mmol) in ether.

Workup

  1. customevaporated in vacuo to dryness
  2. customResidual water was removed
  3. additionaddition and evaporation of toluene
  4. customThe DMF was removed in vacuo
  5. dissolutionthe product was dissolved in acetone
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo
  8. additionthe product was treated with 95% trifluoroactetic acid (TFA) (4 ml)

Sources & evidence

ORD record
ord-9262748457094615b46c91db2ea086e8
Source dataset
uspto-grants-2011_11
Patent number
US08048852B2

Reaction notes

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