4-Methylmorpholine → Nalpha-Boc-Ndelta-Cbz-ornithinol

HRID 269677Notes

Reaction equation

HRID 269677 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:24](O)=[O:25])[NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1CCOCC1.ClC(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([O:8][C:9](=[O:10])[NH:11][CH2:12][CH2:13][CH2:14][C@H:15]([NH:16][C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[CH2:24][OH:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 7269338(2S)-5-{[(benzyloxy)carbonyl]amino}-2-{[(tert-butoxy)carbonyl]amino}pentanoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 11772551Nalpha-Boc-Ndelta-Cbz-ornithinol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Preparation takes place in analogy to Example 83A from 1.0 g (2.73 mmol) of N5-[(benzyloxy)carbonyl]-N2-(tert-butoxycarbonyl)-L-ornithine in 35 ml of tetrahydrofuran with 0.276 g (2.73 mmol) of 4-methylmorpholine, 0.296 g (2.73 mmol) of ethyl chloroformate and 5.5 ml (5.5 mmol) of a 1M solution of lithium aluminum hydride in tetrahydrofuran. The product is purified by preparative HPLC (Kromasil, mobile phase acetonitrile/0.25% aqueous trifluoroacetic acid 5:95→95:5).

Workup

  1. customPreparation
  2. customThe product is purified by preparative HPLC (Kromasil, mobile phase acetonitrile/0.25% aqueous trifluoroacetic acid 5:95→95:5)

Sources & evidence

ORD record
ord-fcf9ba16ed3747e2a5aa65d77be96452
Source dataset
uspto-grants-2008_11
Patent number
US07446102B2

Reaction notes

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