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

HRID 2288923Notes

Reaction equation

HRID 2288923 reaction equation
N#N.[ClH:3].C([O:8][C:9](=[O:27])[C@H:10]([CH2:12][CH2:13][CH2:14][NH:15][CH2:16][O:17][CH:18]=[N:19]C(OC(C)(C)C)=O)[NH2:11])(C)(C)C.Cl>O1CCOCC1>[ClH:3].[ClH:3].[NH:19]=[CH:18][O:17][CH2:16][NH:15][CH2:14][CH2:13][CH2:12][C@@H:10]([C:9]([OH:27])=[O:8])[NH2:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86755535N2 (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-9e301030c4ef4d6992ba1d7dd6d774c2
Source dataset
uspto-grants-2000_07
Patent number
US06090846

Reaction notes

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