Nalpha-Boc-Ndelta-Cbz-ornithinol → tert-butyl[(1S)-4-amino-1-(hydroxymethyl)butyl]carbamate

HRID 269678Notes

Reaction equation

HRID 269678 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][C@H:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15][OH:16])C1C=CC=CC=1>C(O)C.[Pd]>[C:21]([O:20][C:18](=[O:19])[NH:17][C@H:14]([CH2:15][OH:16])[CH2:13][CH2:12][CH2:11][NH2:10])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 1

HCID 11772551Nalpha-Boc-Ndelta-Cbz-ornithinol

Product 1

HCID 88986916tert-butyl[(1S)-4-amino-1-(hydroxymethyl)butyl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Preparation takes place in analogy to Example 81A from 0.232 g (0.66 mmol) of benzyl{(4S)-4-[(tert-butoxycarbonyl)amino]-5-hydroxypentyl}carbamate (Example 246A) in 50 ml of ethanol with the addition of 23 mg of palladium on activated carbon (10%).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-f93464bae592471ca7a7e4587f1faab5
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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