(R)-N5-(Cbz)-N2-(Diphenylacetyl)-N-methyl-(R)-N-(1-phenylethyl)ornithine amide → (R)-N2-(Diphenylacetyl)-N-methyl-(R)-N-(1-phenylethyl)ornithine amide

HRID 366078Notes

Reaction equation

HRID 366078 reaction equation
C([NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([C:32]([N:34]([CH3:43])[C@@H:35]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[CH3:36])=[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:2]>[Pd].CC(O)=O>[OH-:2].[NH4+:11].[C:25]1([CH:18]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:17]([NH:16][C@@H:15]([C:32]([N:34]([CH3:43])[C@@H:35]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH3:36])=[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 131722084(R)-N5-(Cbz)-N2-(Diphenylacetyl)-N-methyl-(R)-N-(1-phenylethyl)ornithine amide

Product 2

HCID 14923Ammonium HydroxideHCID 131722085(R)-N2-(Diphenylacetyl)-N-methyl-(R)-N-(1-phenylethyl)ornithine amideYield 193.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Prepared according to the method described in Example 1(e) above from (R)-N5 -(Cbz)-N2 -(diphenylacetyl)-N-methyl-(R)-N-(1-phenylethyl)ornithine amide (1.6 g; 2.8 mmol; from step (b) above), 10% Pd/C (w/w; 100 mg), HOAc (75 mL), overnight reaction time. The crude acetate salt was purified by chromatography on silica gel with EtOAc, then CHCl3 :MeOH:concentrated ammonium hydroxide (6:3:1) to provide 1.2 g (98%) of the sub-title compound.

Workup

  1. customPrepared
  2. customThe crude acetate salt was purified by chromatography on silica gel with EtOAc

Sources & evidence

ORD record
ord-da8d80a248e6447ca689f2ec376c10af
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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