Hydrochloric Acid → N5-(iminomethoxymethyl)-L-ornithine dihydrochloride

HRID 379078Notes

Reaction equation

HRID 379078 reaction equation
[ClH:1].C([O:6][C:7](=[O:25])[C@H:8]([CH2:17][CH2:18][CH2:19][NH:20][CH2:21][O:22][CH:23]=[NH:24])[NH:9]C(OC(C)(C)C)=O)(C)(C)C.Cl>O1CCOCC1>[ClH:1].[ClH:1].[NH:24]=[CH:23][O:22][CH2:21][NH:20][CH2:19][CH2:18][CH2:17][C@@H:8]([C:7]([OH:25])=[O:6])[NH2:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86583874N2-(tert-butoxycarbonyl)-N5-(iminomethoxymethyl)-L-ornithine tert-butyl ester hydrochloride

Product 1

HCID 86583873N5-(iminomethoxymethyl)-L-ornithine dihydrochlorideYield 206.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
22 °C

Procedure

A solution of 0.75 g (1.96 mmol) N2-(tert-butoxycarbonyl)-N5-(iminomethoxymethyl)-L-ornithine tert-butyl ester hydrochloride in 2 mL dioxane at 0° C. was treated with 15 mL of 4N hydrochloric acid in dioxane solution. The solution was stirred overnight at 22° C., concentrated to a crude paste, and freeze-dried from 8 mL of water. The product was freeze-dried a second time to yield 0.53 g N5-(iminomethoxymethyl)-L-ornithine dihydrochloride. The product analyzed solvated with an additional 0.2 molar hydrochloric acid 0.1 molar water, and 0.3 molar dioxane.

Workup

  1. concentrationconcentrated to a crude paste
  2. dry with materialfreeze-dried from 8 mL of water
  3. customThe product was freeze-dried a second time

Sources & evidence

ORD record
ord-eeca8fc9ad864c63b52dab6f9ab88708
Source dataset
uspto-grants-2001_10
Patent number
US06297276B1

Reaction notes

Loading…