Hydrochloric Acid → alpha-(Difluoromethyl)arginine

HRID 638398

Reaction equation

HRID 638398 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 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-c047f1b2107248efa5cf78f9eeebf7f6
Source dataset
uspto-grants-1985_12
Patent number
US04560795

Linked notes

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