beta-benzyl N-benzyloxycarbonyl-L-aspartyl-D-alanine amide → L-aspartyl-D-alanine amide monohydrate

HRID 596802Notes

Reaction equation

HRID 596802 reaction equation
C([CH:8]([C:29](=[O:31])[OH:30])[C@@H:9]([C:21]([NH:23][C@@H:24]([C:26]([NH2:28])=[O:27])[CH3:25])=[O:22])[NH:10]C(OCC1C=CC=CC=1)=[O:12])C1C=CC=CC=1.[H][H]>[Pd].C(O)(=O)C>[OH2:12].[NH2:10][C@H:9]([C:21]([NH:23][C@@H:24]([C:26]([NH2:28])=[O:27])[CH3:25])=[O:22])[CH2:8][C:29](=[O:30])[OH:31]

Participants

5

Reactant 2

HCID 53846268beta-benzyl N-benzyloxycarbonyl-L-aspartyl-D-alanine amideHCID 178418361HCID 178418361, compound

Product 1

HCID 22796342L-aspartyl-D-alanine amide monohydrate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 61.10 parts of β-benzyl N-benzyloxycarbonyl-L-aspartyl-D-alanine amide in 800 parts by volume of 75% acetic acid is added 6 parts of palladium black metal catalyst, and the resulting mixture is shaken with hydrogen at room temperature at atmospheric pressure for about 6.5 hours. The catalyst is removed by filtration, and the solvents removed by distillation under reduced pressure to obtain an oil. This oil is triturated with water and stripped under reduced pressure three times to afford a solid. The solid is then triturated with ethanol, filtered, and dried under vacuum to yield L-aspartyl-D-alanine amide monohydrate. This product is represented by the following structural formula.

Workup

  1. customThe catalyst is removed by filtration
  2. customthe solvents removed by distillation under reduced pressure
  3. customto obtain an oil
  4. customThis oil is triturated with water
  5. customto afford a solid
  6. customThe solid is then triturated with ethanol
  7. filtrationfiltered
  8. customdried under vacuum

Sources & evidence

ORD record
ord-04d882ec8cb74848a57baf6434412d8b
Source dataset
uspto-grants-1977_03
Patent number
US04012367

Reaction notes

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