Hydrochloric Acid → HCID 178459329, compound

HRID 2288925Notes

Reaction equation

HRID 2288925 reaction equation
N#N.[ClH:3].C([O:8][C:9](=[O:29])[C@H:10]([CH2:12][CH2:13][CH2:14][NH:15][C:16](=[N:21]C(OC(C)(C)C)=O)[O:17][CH:18]([CH3:20])[CH3:19])[NH2:11])(C)(C)C.Cl>O1CCOCC1>[ClH:3].[ClH:3].[NH:21]=[C:16]([O:17][CH:18]([CH3:20])[CH3:19])[NH:15][CH2:14][CH2:13][CH2:12][C@@H:10]([C:9]([OH:29])=[O:8])[NH2:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178459326HCID 178459326, compound

Product 1

HCID 178459329HCID 178459329, compoundYield 271.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a 0° C. stirred solution of 0.54 g (1.32 mmol) N2 -(tert-butoxycarbonyl) N5 -(iminoisopropoxymethyl)-L-ornithine tert-butyl ester hydrochloride in 2 ml dioxane was added 10 mL of 4N hydrochloric acid in dioxane solution. The solution was stirred 14 h leaving a pale yellow precipitate. The dioxane was removed under reduced pressure and the residue suspended in ether. After stirring for 3 h, the ether was decanted and the solids dried under vacuum to give 0.52 g N5 -(iminoisopropoxymethyl)-L-ornithine dihydrochloride. TLC (silica gel, ammonium hydroxide:methanol/1:25) Rf=0.27.

Workup

  1. customleaving a pale yellow precipitate
  2. customThe dioxane was removed under reduced pressure
  3. stirringAfter stirring for 3 h
  4. customthe ether was decanted
  5. customthe solids dried under vacuum

Sources & evidence

ORD record
ord-f469e509d3204a9d86c9c023e8ed3055
Source dataset
uspto-grants-2000_07
Patent number
US06090846

Reaction notes

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