Citric Acid → N-acetylmelphalan

HRID 2105114Notes

Reaction equation

HRID 2105114 reaction equation
[CH:1]1[C:6]([CH2:7][C@H:8]([NH2:12])[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=[C:3]([N:13]([CH2:17][CH2:18][Cl:19])[CH2:14][CH2:15][Cl:16])[CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:26](OC(=O)C)(=[O:28])[CH3:27].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.O1CCOCC1>[CH3:27][C:26]([NH:12][CH:8]([C:9]([OH:11])=[O:10])[CH2:7][C:6]1[CH:5]=[CH:4][C:3]([N:13]([CH2:14][CH2:15][Cl:16])[CH2:17][CH2:18][Cl:19])=[CH:2][CH:1]=1)=[O:28]

Participants

7

Reactant 4

HCID 311Citric AcidHCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 460612Melphalan

Product 1

HCID 14399N-acetylmelphalan

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

600 mg of melphalan (63) is suspended in 25 ml of water containing 500 mg of sodium carbonate. 10 ml of dioxane is added and 1 ml of acetic anhydride. After stirring at ambient temperature for 1 h citric acid is added and the mixture extracted with ethyl acetate. After washing with water and brine the organic phase is dried (sodium sulfate) and concentrated in vacuum. Removal of all volatiles yields the crude N-acetylmelphalan that is carried on to the next step without further purification.

Workup

  1. additionis added
  2. extractionthe mixture extracted with ethyl acetate
  3. washAfter washing with water and brine the organic phase
  4. dry with materialis dried (sodium sulfate)
  5. concentrationconcentrated in vacuum
  6. customRemoval of all volatiles

Sources & evidence

ORD record
ord-cfd1f95d9a2c4c539bcd56b4cb0d263c
Source dataset
uspto-grants-2009_08
Patent number
US07579324B2

Reaction notes

Loading…