(R)-beta-aminophenethyl alcohol → (R)-N2-(Boc)-N5-(Cbz)-(R)-N-(2-Hydroxy-1-phenylethyl)ornithine amide

HRID 366058Notes

Reaction equation

HRID 366058 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.[CH:36]1[CH:41]=[CH:40][C:39]([C@@H:42]([NH2:45])[CH2:43][OH:44])=[CH:38][CH:37]=1>C(Cl)Cl>[C:14]([NH:13][C@@H:12]([C:11]([NH:45][C@H:42]([C:39]1[CH:40]=[CH:41][CH:36]=[CH:37][CH:38]=1)[CH2:43][OH:44])=[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 2724025(R)-beta-aminophenethyl alcoholHCID 54461433Nalpha-Boc-Ndelta-Cbz-(R)-ornithine o-nitrophenyl ester

Product 1

HCID 131722061(R)-N2-(Boc)-N5-(Cbz)-(R)-N-(2-Hydroxy-1-phenylethyl)ornithine amideYield 69.8%

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 (5.0 g; 11.5 mmol; see Example 4(a) above), (R)-(-)-phenylglycinol (1.58 g; 11.5 mmol) and 160 mL of CH2Cl2, yielding 3.9 g of the sub-title compound as a white solid.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-92e6a83c76064f25a849826c350fee0d
Source dataset
uspto-grants-2000_10
Patent number
US06127414

Reaction notes

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