(R)-N5-(Cbz)-N2-(Diphenylacetyl)-(S)-N-(2-hydroxy-1-phenylethyl)-ornithine amide → (R)-N2-(Diphenylacetyl)-(S)-N-(2-hydroxy-1-phenylethyl)ornithine amide

HRID 366055Notes

Reaction equation

HRID 366055 reaction equation
C([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:32]([NH:34][C@H:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[CH2:36][OH:37])=[O:33])[NH:16][C:17](=[O:31])[CH:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(OCC1C=CC=CC=1)=O>CO.Cl.[Pd]>[C:25]1([CH:18]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:17]([NH:16][C@H:15]([C:32]([NH:34][C@H:35]([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[CH2:36][OH:37])=[O:33])[CH2:14][CH2:13][CH2:12][NH2:11])=[O:31])[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 1

HCID 86755916(R)-N5-(Cbz)-N2-(Diphenylacetyl)-(S)-N-(2-hydroxy-1-phenylethyl)-ornithine amide

Product 1

HCID 86755915(R)-N2-(Diphenylacetyl)-(S)-N-(2-hydroxy-1-phenylethyl)ornithine amideYield 84.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Prepared according to the method described in Example 1(e) above from a batch of (R)-N5 -(Cbz)-N2 -(diphenylacetyl)-(S)-N-(2-hydroxy-1-phenyl-ethyl)ornithine amide (1.78 g; from step (c) above) and 10% Pd/C (200 mg) in 100 mL of MeOH and 1.0 mL of HCl (conc.), yielding 1.15 g of the sub-title compound as a white foam.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f5bc32957728487084c64335f3635610
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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