Benzyl Bromide → HCID 70045798, compound

HRID 487423Notes

Reaction equation

HRID 487423 reaction equation
[ClH:1].[C:2]([CH2:5][C@@H:6]1[NH:11][CH2:10][CH2:9][N:8]([CH2:12][C:13]([OH:15])=[O:14])[C:7]1=[O:16])(=[O:4])[NH2:3].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])O.[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C)C=O.C(OCC)(=O)C.Cl.C(OCC)(=O)C.CCOCC.O.O1CCOCC1>[ClH:1].[CH2:28]([O:14][C:13](=[O:15])[CH2:12][N:8]1[CH2:9][CH2:10][NH:11][C@@H:6]([CH2:5][C:2](=[O:4])[NH2:3])[C:7]1=[O:16])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

11

Reactant 4

HCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 516893Potassium BicarbonateHCID 70043717HCID 70043717, compound

Product 1

HCID 70045798HCID 70045798, compoundYield 50%

Reagents, catalysts & solvents 6

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolventHCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

To a mixture of 1.8 g of (S)-3-carbamoylmethyl-2-oxopiperazine-1-acetic acid hydrochloride, 3.0 g of sodium carbonate, 20 ml of dioxane and 20 ml of water was added, while stirring vigorously, 2.0 g of di-t-butyl bicarbonate. The mixture was stirred vigorously for 2 hours at 0° C. The reaction mixture was concentrated to half of its original volume. The concentrate was washed with ether and there was added 20 ml of a 10% aqueous solution of potassium hydrogensulfate, followed by extraction with methylene chloride. The extract solution was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to give an oily product. The oily product was dissolved in 10 ml of dimethylformamide, to which were added 720 mg of potassium hydrogencarbonate and 1.0 g of benzyl bromide. The mixture was stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate, washed with water and dried over anhydrous magnesium sulfate, followed by concentration under reduced pressure to give a crude product. The crude product was dissolved in 30 ml of 2N HCl-ethyl acetate, and the solution was stirred for one hour at room temperature. The reaction mixture was concentrated under reduced pressure to give an oily product, which was processed with ether to afford 1.0 g of the title compound as amorphous powder.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred vigorously for 2 hours at 0° C
  3. concentrationThe reaction mixture was concentrated to half of its original volume
  4. washThe concentrate was washed with ether and there
  5. additionwas added 20 ml of a 10% aqueous solution of potassium hydrogensulfate
  6. extractionfollowed by extraction with methylene chloride
  7. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto give an oily product
  10. stirringThe mixture was stirred for 12 hours at room temperature
  11. washwashed with water
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationfollowed by concentration under reduced pressure
  14. customto give a crude product
  15. stirringthe solution was stirred for one hour at room temperature
  16. concentrationThe reaction mixture was concentrated under reduced pressure
  17. customto give an oily product, which

Sources & evidence

ORD record
ord-58cdf2ba0b8e44eb966a165bb1493e36
Source dataset
uspto-grants-1994_03
Patent number
US05294713

Reaction notes

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