(R)-N2-(Boc)-N5-(Cbz)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide → (R)-N2-(Boc)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide

HRID 366089Notes

Reaction equation

HRID 366089 reaction equation
[C:1]([NH:8][C@@H:9]([C:24]([NH:26][C@@H:27]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[CH3:28])=[O:25])[CH2:10][CH2:11][CH2:12][NH:13]C(OCC1C=CC=CC=1)=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H][H]>CO.[Pd]>[C:1]([NH:8][C@@H:9]([C:24]([NH:26][C@@H:27]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[CH3:28])=[O:25])[CH2:10][CH2:11][CH2:12][NH2:13])([O:3][C:4]([CH3:7])([CH3:5])[CH3:6])=[O:2]

Participants

5

Reactant 2

HCID 131722030(R)-N2-(Boc)-N5-(Cbz)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amideHCID 178418361HCID 178418361, compound

Product 1

HCID 131722103(R)-N2-(Boc)-(R)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amideYield 88.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (R)-N2 -(Boc)-N5 -(Cbz)-(R)-N-[1-(4-hydroxyphenyl)-ethyl]ornithine amide (66.26 g; 139 mmol; see Example 4(b) above) in methanol (400 mL) was added 10% Pd/C (w/w; 3.53 g). After stirring for 18 h under 1 atmosphere of hydrogen the reaction was filtered through Celite to remove the catalyst and the filtrate was concentrated under reduced pressure to afford the sub-title compound as a white foam (43.2 g, 123 mmol).

Workup

  1. filtrationwas filtered through Celite
  2. customto remove the catalyst
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-00c9ca4cfc424db4915128d765058c2d
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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