Hydrogen chloride-ethyl acetate → (R)-N5-(Cbz)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide hydrochloride

HRID 366074Notes

Reaction equation

HRID 366074 reaction equation
C([NH:8][C@H:9]([C:24]([NH:26][C@@H:27]([C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)[CH3:28])=[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>C(OCC)(=O)C>[ClH:36].[C:14]([NH:13][CH2:12][CH2:11][CH2:10][C@@H:9]([C:24]([NH:26][C@@H:27]([C:29]1[CH:30]=[CH:31][C:32]([OH:35])=[CH:33][CH:34]=1)[CH3:28])=[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 86755920(R)-N2-(Boc)-N5-(Cbz)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide

Product 1

HCID 86755918(R)-N5-(Cbz)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared according to the method described in Example 1(b) above from (R)-N2 -(Boc)-N5 -(Cbz)-(S)-N-[1-(4-hydroxyphenyl)ethyl]ornithine amide (5.1 g; from step (a) above), ethyl acetate (100 mL) and HCl/EtOAc (100 mL) yielding, after isolation, 3.3 g of the sub-title compound as a tan solid.

Workup

  1. customPrepared
  2. customyielding

Sources & evidence

ORD record
ord-c7fc325e3e4f41df917ad49949ed72a3
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

Loading…