Acetic Acid → (R)-N2-(Diphenylacetyl)-(S)-N-(1-phenylethyl)ornithine amide hydrochloride

HRID 366046Notes

Reaction equation

HRID 366046 reaction equation
C([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:32]([NH:34][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.CC(O)=O.[ClH:47]>[Pd].CO>[ClH:47].[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]([NH:34][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

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 131722048(R)-N5-(Cbz)-N2-(diphenylacetyl)-(S)-N-(1-phenylethyl)ornithine amide

Product 1

HCID 131722046(R)-N2-(Diphenylacetyl)-(S)-N-(1-phenylethyl)ornithine amide hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Prepared according to the method described in Example 1(e) above from (R)-N5 -(Cbz)-N2 -(diphenylacetyl)-(S)-N-(1-phenylethyl)ornithine amide (2.0 g; 3.5 mmol; from step (b) above), 10% Pd/C (w/w; 150 mg), HOAc (100 mL; instead of MeOH), overnight reaction time. The crude acetate salt was converted to the sub-title hydrochloride and was used without further purification.

Workup

  1. customPrepared
  2. customwas used without further purification

Sources & evidence

ORD record
ord-97a8e9324d2f40f4ac14d0bab09bf6f1
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

Loading…