Hydrogen chloride-ethyl acetate → (R)-N5-(Cbz)-(S)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-ornithine amide hydrochloride

HRID 366065Notes

Reaction equation

HRID 366065 reaction equation
C([NH:8][C@H:9]([C:24]([NH:26][C@H:27]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[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:38].CCOC(C)=O>CCOC(C)=O>[ClH:38].[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][C:33]([O:36][CH3:37])=[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 131722069(R)-N2-(Boc)-N5-(Cbz)-(S)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]ornithine amide

Product 1

HCID 131722070(R)-N5-(Cbz)-(S)-N-[2-hydroxy-1-(4-methoxyphenyl)ethyl]-ornithine amide hydrochloride

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Prepared according to the method described in Example 1(b) above from crude (R)-N2 -(Boc)-N5 -(Cbz)-(S)-N-[2-hydroxy-l-(4-methoxyphenyl)ethyl]-ornithine amide (4.0 g; from step (a) above), EtOAc (100 mL) and HCl/EtOAc (100 mL), 18 hours reaction time. The hydrochloride salt was precipitated by the addition of diethyl ether, collected and dried to give the sub-title compound as a white solid (2.3 g).

Workup

  1. customPrepared
  2. customThe hydrochloride salt was precipitated by the addition of diethyl ether
  3. customcollected
  4. customdried

Sources & evidence

ORD record
ord-1dac5ae6504347d18da74c2f63b94d74
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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