Nalpha-Boc-Ndelta-Cbz-(R)-ornithine o-nitrophenyl ester → (R)-N2-(Boc)-N5-(Cbz)-(R)-N-[1-(4-Benzyloxyphenyl)ethyl]ornithine amide

HRID 366081Notes

Reaction equation

HRID 366081 reaction equation
[N+](C1C=CC=CC=1O[C:11](=[O:35])[C@@H:12]([CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:26])[NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])([O-])=O.Cl.[CH2:37]([O:44][C:45]1[CH:53]=[CH:52][C:48]([C@H:49]([NH2:51])[CH3:50])=[CH:47][CH:46]=1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C(Cl)Cl>[C:14]([NH:13][C@@H:12]([C:11]([NH:51][C@@H:49]([C:48]1[CH:52]=[CH:53][C:45]([O:44][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)=[CH:46][CH:47]=1)[CH3:50])=[O:35])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)=[O:26])([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15]

Participants

4

Reactant 2

HCID 54461433Nalpha-Boc-Ndelta-Cbz-(R)-ornithine o-nitrophenyl esterHCID 70140442(1R)-1-[4-(benzyloxy)phenyl]ethan-1-amine hydrochloride

Product 1

HCID 131722089(R)-N2-(Boc)-N5-(Cbz)-(R)-N-[1-(4-Benzyloxyphenyl)ethyl]ornithine amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Prepared according to the method described in Example 4(b) above from Nα -Boc-Nδ -Cbz-(R)-ornithine-o-nitrophenyl ester (3.11 g; 6.37 mmol), (R)-4-benzyloxy-α-methylbenzylamine hydrochloride (1.68 g; 6.37 mmol), TEA (1.94 g; 19.10 mmol) and CH2Cl2 (200 mL), 18 hours reaction time. The resultant yellow solution was concentrated to afford the crude sub-title compound which was used directly in the next step.

Workup

  1. customPrepared
  2. concentrationThe resultant yellow solution was concentrated

Sources & evidence

ORD record
ord-0576b098817646178926dc79835565c4
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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