Hydrochloric Acid → (R)-N2-(Diphenylacetyl)-(S)-N-[2-hydroxy-l-(4-methoxyphenyl)-ethyl]ornithine amide hydrochloride

HRID 366067Notes

Reaction equation

HRID 366067 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][C:41]([O:44][CH3:45])=[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.[ClH:46]>[Pd].CO>[ClH:46].[C:19]1([CH:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:17]([NH:16][C@H:15]([C:32]([NH:34][C@H:35]([C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[CH:40][CH:39]=2)[CH2:36][OH:37])=[O:33])[CH2:14][CH2:13][CH2:12][NH2:11])=[O:31])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131722072(R)-N5-(Cbz)-N2-(Diphenylacetyl)-(S)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]ornithine amide

Product 1

HCID 131722073(R)-N2-(Diphenylacetyl)-(S)-N-[2-hydroxy-l-(4-methoxyphenyl)-ethyl]ornithine amide hydrochloride

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

Prepared according to the method described in Example 1(e) above from (R)-N5 -(Cbz)-N2 -(diphenylacetyl)-(S)-N-[2-hydroxy-1 -(4-methoxyphenyl)-ethyl]ornithine amide (2.85 g; from step (c) above), 10% Pd/C (1.40 g), MeOH (200 mL) and concentrated HCl (2 mL) under hydrogen for 6 hours to give the crude product as a solid (2.6 g). Pure sub-title compound was obtained by crystallization from MeOH:diethyl ether to give a white solid (1.58 g).

Workup

  1. customPrepared
  2. customto give the crude product as a solid (2.6 g)

Sources & evidence

ORD record
ord-66ba0f4986044fbe979d07358c38eeb1
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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