Phosphoric Acid → N-neohexyl-L-aspartic anhydride

HRID 1421638Notes

Reaction equation

HRID 1421638 reaction equation
C(OC([N:11]([CH2:20][CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C@H:12]([C:17]([OH:19])=[O:18])[CH2:13][C:14](O)=[O:15])=O)C1C=CC=CC=1.P(=O)(O)(O)O>C(OC(=O)C)(=O)C>[CH2:20]([NH:11][C@@H:12]1[C:17](=[O:19])[O:18][C:14](=[O:15])[CH2:13]1)[CH2:21][C:22]([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 1004Phosphoric AcidHCID 21969156HCID 21969156, compound

Product 1

HCID 11217864N-neohexyl-L-aspartic anhydride

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A solution of N-benzyloxycarbonyl-N-neohexyl-L-aspartic acid, in acetic anhydride with a catalytic amount of phosphoric acid, is heated at reflux for 0.5 to 5 hours, is cooled to room temperature, and is concentrated under reduced pressure, with heating. The residual material is dissolved in water, then neutralized with aqueous sodium hydroxide. The resulting precipitate is collected by vacuum filtration, and is recrystallized to provide substantially pure N-neohexyl-L-aspartic anhydride.

Workup

  1. temperatureat reflux for 0.5 to 5 hours
  2. concentrationis concentrated under reduced pressure
  3. temperaturewith heating
  4. dissolutionThe residual material is dissolved in water
  5. filtrationThe resulting precipitate is collected by vacuum filtration
  6. customis recrystallized

Sources & evidence

ORD record
ord-3b9ffdcd06e94c2bbc129249bace3c80
Source dataset
uspto-grants-2000_06
Patent number
US06077962

Reaction notes

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