Hydrochloric Acid → HCID 21363107, compound

HRID 986871Notes

Reaction equation

HRID 986871 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C@H:11]([C:27]([OH:29])=[O:28])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16]C(OCC2C=CC=CC=2)=O)=[CH:6][CH:5]=1)([O-])=O.O.[ClH:31]>C(O)C.[Pd]>[ClH:31].[ClH:31].[ClH:31].[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C@H:11]([C:27]([OH:29])=[O:28])[CH2:12][CH2:13][CH2:14][CH2:15][NH2:16])=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86759188HCID 86759188, compound

Product 1

HCID 21363107HCID 21363107, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

0.40 g (1 mmol) of Nα-(4-nitrophenyl)-Nε-(benzyloxycarbonyl)-L-lysine is dissolved in 20 ml of ethanol, 5 ml of water and 0.5 ml (3.5 eq) of 5N hydrochloric acid in a 250 ml glass reactor (Paar apparatus). 0.5 g of palladium-on-charcoal (50% moisture and 10% active) is then introduced. The mixture is hydrogenated under a pressure of approximately 2.76×105 Pa for 45 minutes and at a temperature of 12° C. After filtration through celite, the filtrate is evaporated. The purplish oily residue is taken up in ethanol and precipitated from a large volume of acetone with stirring. After filtration, 0.3 g of a white crystalline powder is obtained, i.e. a final yield of 93%.

Workup

  1. filtrationAfter filtration through celite
  2. customthe filtrate is evaporated
  3. customprecipitated from a large volume of acetone
  4. filtrationAfter filtration

Sources & evidence

ORD record
ord-b99bbff486b146b7a2bd1cc8fdb6fe7c
Source dataset
uspto-grants-2003_10
Patent number
US06630004B1

Reaction notes

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