Hydrochloric Acid → HCID 178459329, compound

HRID 1975907Notes

Reaction equation

HRID 1975907 reaction equation
[ClH:1].C([O:6][C:7](=[O:27])[C@H:8]([CH2:17][CH2:18][CH2:19][NH:20][C:21](=[NH:26])[O:22][CH:23]([CH3:25])[CH3:24])[NH:9]C(OC(C)(C)C)=O)(C)(C)C.Cl>O1CCOCC1>[ClH:1].[ClH:1].[NH:26]=[C:21]([O:22][CH:23]([CH3:25])[CH3:24])[NH:20][CH2:19][CH2:18][CH2:17][C@@H:8]([C:7]([OH:27])=[O:6])[NH2:9]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178459328HCID 178459328, 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-6b926be10c494655a38740f05454c2e9
Source dataset
uspto-grants-2001_05
Patent number
US06225305B1

Reaction notes

Loading…