Hydrogen chloride-ethyl acetate → (R)-N5-(Cbz)-(R)-N-(2-hydroxy-1-phenylethyl)ornithine amide hydrochloride

HRID 366059Notes

Reaction equation

HRID 366059 reaction equation
C([NH:8][C@@H:9]([C:24]([NH:26][C@H:27]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:28][OH:29])=[O:25])[CH2:10][CH2:11][CH2:12][NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])(OC(C)(C)C)=O.[ClH:36].CCOC(C)=O>CO>[ClH:36].[C:14]([NH:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:24]([NH:26][C@H:27]([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[CH2:28][OH:29])=[O:25])[NH2:8])([O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)=[O:15]

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 131722061(R)-N2-(Boc)-N5-(Cbz)-(R)-N-(2-Hydroxy-1-phenylethyl)ornithine amide

Product 1

HCID 131722062(R)-N5-(Cbz)-(R)-N-(2-hydroxy-1-phenylethyl)ornithine amide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared according to the method described in Example 1(b) above from (R)-N2 -(Boc)-N5 -(Cbz)-(R)-N-(2-hydroxy-1-phenylethyl)ornithine amide (3.8 g; 7.82 mmol; from step (a) above), 50 mL of MeOH and 100 mL of HCl/EtOAc, isolating 2.68 g of the sub-title compound as white crystals.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-cd8aeaa7d9b94f74ab08a36fb09c2ff9
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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