Hydrochloric Acid → alpha-(Difluoromethyl)arginine

HRID 2413282

Reaction equation

HRID 2413282 reaction equation
Cl.O.[F:3][CH:4]([F:14])[C:5]([NH2:13])([CH2:9][CH2:10][CH2:11][NH2:12])[C:6]([OH:8])=[O:7].Br.C([NH+:18]=[C:19]([NH2:21])S)C.Cl>[OH-].[Na+]>[F:3][CH:4]([F:14])[C:5]([NH2:13])([CH2:9][CH2:10][CH2:11][NH:12][C:19]([NH2:21])=[NH:18])[C:6]([OH:8])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 441361Ornithine, 2-(difluoromethyl)-, hydrochloride, hydrate (1:1:1)HCID 178419565[amino(sulfanyl)methylidene]-ethylazanium;hydrobromide

Product 1

HCID 178512962alpha-(Difluoromethyl)arginine

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 2-difluoromethyl-2,5-diamino-pentanoic acid monohydrate monohydrochloride (5 g or 21.13 mmole) in NaOH 2M (8.5 ml) is added at once ethylthiouronium hydrobromide (7.82 g or 42.26 mmole). The pH of the solution is adjusted to 10.5 with NaOH 2M and maintained to that value for 4 days. The reaction mixture is then neutralized to pH=7 with 1M HCl and concentrated under reduced pressure. The residue is passed on an Amberlite IR 120 H+ form column. Elution with NH4OH 2M affords 2-difluoromethyl-2-amino-5-guanidinopentanoic acid which is recrystallized from H2O/EtOH (2.3 g) m.p. 257° C.

Workup

  1. temperaturemaintained to that value for 4 days
  2. concentrationconcentrated under reduced pressure
  3. washElution with NH4OH 2M

Sources & evidence

ORD record
ord-03b12917c33a4013b9aba43ca3b6ebe9
Source dataset
uspto-grants-1985_01
Patent number
US04496588

Linked notes

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