Hydrochloric Acid → Ndelta-Boc-Nalpha-Methylornithine 2-(4-Hydroxyphenyl)ethylamide

HRID 1067076Notes

Reaction equation

HRID 1067076 reaction equation
[H][H].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:12][C:13](=[O:35])[C@H:14]([CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:15](CC2C=CC=CC=2)[CH3:16])=[CH:6][CH:5]=1.Cl>C(O)C.[Pd]>[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:12][C:13](=[O:35])[C@H:14]([CH2:24][CH2:25][CH2:26][NH:27][C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[NH:15][CH3:16])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 131722651Nalpha-Benzyl-Ndelta-Boc-Nalpha-Methylornithine 2-(4-Hydroxyphenyl)ethylamideHCID 178418361HCID 178418361, compound

Product 1

HCID 131722652Ndelta-Boc-Nalpha-Methylornithine 2-(4-Hydroxyphenyl)ethylamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrogen gas was bubbled through a solution of Nα-benzyl-Nδ-Boc-Nα-methylornithine 2-(4-hydroxyphenyl)ethylamide (A) (540 mg) in ethanol (20 ml) in the presence of 1 eq. of conc. hydrochloric acid (1.30 ml) and 5% palladium-on-charcoal (50 mg). After disappearance of starting material, as determined by thin-layer chromatography, the reaction mixture is filtered through a 0.45 μm nylon pad and concentrated in vacuo.

Workup

  1. filtrationthe reaction mixture is filtered through a 0.45 μm nylon pad
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-401657bde251441793ffbd96a1591f47
Source dataset
uspto-grants-2001_06
Patent number
US06245746B1

Reaction notes

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