1-Hydroxybenzotriazole → Nalpha-Fmoc-Ndelta-Boc-L-ornithine Methyl Ester

HRID 11870Notes

Reaction equation

HRID 11870 reaction equation
[C:1]([NH:18][C@H:19]([C:31]([OH:33])=[O:32])[CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2].[CH3:34]CN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CO>[CH3:34][O:32][C:31](=[O:33])[C@H:19]([CH2:20][CH2:21][CH2:22][NH:23][C:24]([O:26][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:25])[NH:18][C:1]([O:3][CH2:4][CH:5]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)=[O:2]

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2756114(2S)-5-(((tert-butoxy)carbonyl)amino)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)pentanoic acid

Product 1

HCID 86592271Nalpha-Fmoc-Ndelta-Boc-L-ornithine Methyl EsterYield 102.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Commercially available Nα-Fmoc-Nδ-Boc-L-ornithine (1.00 g), WSCI hydrochloride (0.633 g), and HOBt (0.446 g) were reacted in methanol (20 ml) for 23 hours at room temperature. After the reaction, methanol was removed and the residue was extracted with chloroform. The extract was washed with water, saturated aqueous solution of sodium hydrogencarbonate, and saturated brine, and dried over anhydrous sodium sulfate to remove water. Syrup obtained by removing the solvent was purified by silica gel column chromatography (50 g, chloroform/ethyl acetate=5/1) to obtain the title compound (1.06 g) as a white solid.

Workup

  1. customwas removed
  2. extractionthe residue was extracted with chloroform
  3. washThe extract was washed with water, saturated aqueous solution of sodium hydrogencarbonate, and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customto remove water
  6. customSyrup obtained
  7. customby removing the solvent
  8. customwas purified by silica gel column chromatography (50 g, chloroform/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-88c344182a2a4d219be99f9edfe605f7
Source dataset
uspto-grants-2006_08
Patent number
US07098215B2

Reaction notes

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