Water → 2,3-Diaminosuccinic acid

HRID 976020Notes

Reaction equation

HRID 976020 reaction equation
C1C=CC(C[NH:8][CH:9]([C:22]([OH:24])=[O:23])[CH:10]([NH:14]CC2C=CC=CC=2)[C:11]([OH:13])=[O:12])=CC=1.O>C(O)(=O)C.Cl.[Pd]>[CH:9]([NH2:8])([C:22]([OH:24])=[O:23])[CH:10]([NH2:14])[C:11]([OH:13])=[O:12]

Participants

6

Reactant 2

HCID 962WaterHCID 108349D-Aspartic acid, N-(phenylmethyl)-3-((phenylmethyl)amino)-, (3S)-rel-

Product 1

HCID 2872902,3-Diaminosuccinic acid

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

Meso-2,3-bis(benzylamino)succinic acid (9.5 g, 0.029 mol) was dissolved in a mixture of glacial acetic acid (50 ml) and concentrated hydrochloric acid (50 ml). Hydrogenolysis was effected at ambient temperature with 10% palladium on charcoal (1.0 g) as catalyst. The reaction was run until NMR showed that unreacted starting material was no longer present. Water (100 ml) was added and the catalyst was removed by filtration. The filtrate was concentrated (rotavapor) and the residue was dissolved in dilute aqueous sodium hydroxide. pH was adjusted to approximately 5 upon addition of glacial acetic acid. Crystals were filtered off and washed.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated (rotavapor)
  3. dissolutionthe residue was dissolved in dilute aqueous sodium hydroxide
  4. additionpH was adjusted to approximately 5 upon addition of glacial acetic acid
  5. filtrationCrystals were filtered off
  6. washwashed

Sources & evidence

ORD record
ord-3df244c65d6a4c8791d3e502ec0bce96
Source dataset
uspto-grants-1997_03
Patent number
US05610141

Reaction notes

Loading…