Hydrochloric Acid → HCID 54445967, compound

HRID 1086594Notes

Reaction equation

HRID 1086594 reaction equation
[NH2:1][C@H:2]([C:8]([NH:10][CH:11]([C:19]([OH:21])=[O:20])[CH2:12][CH:13]=[CH:14][CH2:15][C:16]([OH:18])=[O:17])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7].Cl>C(O)C.[Pd]>[NH2:1][C@H:2]([C:8]([NH:10][CH:11]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]([OH:18])=[O:17])[C:19]([OH:21])=[O:20])=[O:9])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54098214HCID 54098214, compound

Product 1

HCID 54445967HCID 54445967, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

678 mg of 6-(L-lysylamino) 3-heptenedioic acid prepared as in Example 9 were dissolved at ambient temperature in 70 ml of ethanol and 2.1 ml of N hydrochloric acid and then 140 mg of palladium on active carbon were added, followed by hydrogenation under 1100 millibars for an hour and a half. The residue, after filtering, was evaporated to dryness, rinsed with ethanol then with water, dried and concentrated to dryness under reduced pressure. The residue was dissolved in water, and the pH was adjusted to 6 with ammonium hydroxide. The mixture was purified by passing through Dowex 50 W×8 ion-exchange resin and eluting with water and then with 0.5N ammonia, evaporation to dryness and lyophilized to obtain 566 mg of the expected product with a specific rotation of [α]D =+29°±1.5° (c=0.7% in H2O).

Workup

  1. waitfollowed by hydrogenation under 1100 millibars for an hour
  2. filtrationThe residue, after filtering
  3. customwas evaporated to dryness
  4. washrinsed with ethanol
  5. dry with materialwith water, dried
  6. concentrationconcentrated to dryness under reduced pressure
  7. dissolutionThe residue was dissolved in water
  8. customThe mixture was purified
  9. washeluting with water
  10. customwith 0.5N ammonia, evaporation to dryness

Sources & evidence

ORD record
ord-58b04b9734e2483f9741f015fe207c66
Source dataset
uspto-grants-1991_07
Patent number
US05030715

Reaction notes

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