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

HRID 366082Notes

Reaction equation

HRID 366082 reaction equation
C([NH:8][C@@H:9]([C:24]([NH:26][C@@H:27]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[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:43].CCOC(C)=O>CCOC(C)=O>[ClH:43].[C:14]([NH:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:24]([NH:26][C@@H:27]([C:29]1[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)=[CH:31][CH:30]=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 131722089(R)-N2-(Boc)-N5-(Cbz)-(R)-N-[1-(4-Benzyloxyphenyl)ethyl]ornithine amide

Product 1

HCID 131722090(R)-N5-(Cbz)-(R)-N-[1-(4-Benzyloxyphenyl)ethyl]ornithine amide hydrochlorideYield 75%

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)-(R)-N-[1-(4-benzyloxyphenyl)ethyl]-ornithine amide (6.37 mmol; from step (a) above), EtOAc (200 mL) and HCl/EtOAc (75 mL), 3 hours reaction time. The resultant heterogeneous solution was concentrated to 100 mL, slurried with Et2O and the solids collected and dried to afford the sub-title compound as a white solid (2.5 g; 75%).

Workup

  1. customPrepared
  2. concentrationThe resultant heterogeneous solution was concentrated to 100 mL
  3. customthe solids collected
  4. customdried

Sources & evidence

ORD record
ord-65d27f65176e4e2da68edac123472134
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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