Hydrochloric Acid → HCID 70004345, compound

HRID 986870Notes

Reaction equation

HRID 986870 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[NH2:16])[CH:5]=1)([O-])=O.O.C1CCCCC=1.[ClH:27]>C(O)C.[Pd]>[ClH:27].[ClH:27].[ClH:27].[NH2:1][C:4]1[CH:9]=[CH:8][N:7]=[C:6]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:17]([OH:19])=[O:18])[NH2:16])[CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8079CyclohexeneHCID 70005655HCID 70005655, compound

Product 1

HCID 70004345HCID 70004345, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4 g (14.9 mmol) of Nε-(4-nitro-2-pyridyl)-L-lysine are suspended in 80 ml of ethanol and 8 ml of water in a 100 ml three-necked flask equipped with a thermometer and a reflux condenser. 6 g of palladium-on-charcoal (10% active and 50% moisture) are then introduced, followed by 40 ml of cyclohexene. The mixture is brought to reflux for 2 hours and is then cooled, before being filtered through celite. After having run 60 ml (4 eq) of 1N hydrochloric acid onto the filtrate, the latter is evaporated to dryness and the residue is taken up in ethanol and precipitated from acetone. After filtration, 3.4 g of product are obtained, i.e. a final yield of 66%.

Workup

  1. temperatureto reflux for 2 hours
  2. temperatureis then cooled
  3. filtrationbefore being filtered through celite
  4. customthe latter is evaporated to dryness
  5. customprecipitated from acetone
  6. filtrationAfter filtration, 3.4 g of product
  7. customare obtained

Sources & evidence

ORD record
ord-21ec35f39f42426e867c3087e6fec759
Source dataset
uspto-grants-2003_10
Patent number
US06630004B1

Reaction notes

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