Citric Acid → N-acetylmelphalan

HRID 1807358Notes

Reaction equation

HRID 1807358 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-3df490b43a5a4d49a69a08a3ed117c2a
Source dataset
uspto-grants-2013_01
Patent number
US08357506B2

Reaction notes

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