Hydrochloric Acid → HCID 178454174, compound

HRID 500348Notes

Reaction equation

HRID 500348 reaction equation
[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([OH:16])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:13])[NH:9][N+]([O-])=O.[H][H].Cl>CO.[Pd].CC(O)C>[NH:1]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C@H:2]([C:14]([OH:16])=[O:15])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[NH:9])[NH2:13]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 178418361HCID 178418361, compoundHCID 178454175HCID 178454175, compound

Product 1

HCID 178454174HCID 178454174, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

Boc-hArg(NO2)-Amp (1.5 g) was dissolved in HPLC grade MeOH (120 ml) and to the clear solution was added the Pd—C catalyst (10%, Aldrich). A small stir bar was placed in the flask and the reaction mixture was stirred under a slow stream of hydrogen overnight after incorporating the 5-6N HCl in 2-propanol solution (1.5 ml). After the overnight reaction, the solution was filtered and the solvent evaporated. The white crystalline product was dried under vacuum to give 1.61 g of the Boc-hArg-Amp intermediate product.

Workup

  1. customA small stir bar was placed in the flask
  2. customAfter the overnight reaction
  3. filtrationthe solution was filtered
  4. customthe solvent evaporated
  5. customThe white crystalline product was dried under vacuum

Sources & evidence

ORD record
ord-ede17878d73e44e18e90d8454b2db08f
Source dataset
uspto-grants-2010_08
Patent number
US07772222B2

Reaction notes

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