Hydrochloric Acid → 2-Acetylamino-2-difluoromethyl-5-guanidinopentanoic acid

HRID 2413288Notes

Reaction equation

HRID 2413288 reaction equation
[C:1]([NH:4][C:5]([CH:13]([F:15])[F:14])([CH2:9][CH2:10][CH2:11][NH2:12])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2].Br.C([NH+:19]=[C:20]([NH2:22])S)C.Cl>[OH-].[Na+]>[C:1]([NH:4][C:5]([CH:13]([F:14])[F:15])([CH2:9][CH2:10][CH2:11][NH:12][C:20]([NH2:22])=[NH:19])[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 199663382-Acetylamino-5-amino-2-difluoromethylpentanoic acidHCID 178419565[amino(sulfanyl)methylidene]-ethylazanium;hydrobromide

Product 1

HCID 1784747752-Acetylamino-2-difluoromethyl-5-guanidinopentanoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a solution of 2-acetylamino-5-amino-2-difluoromethylpentanoic acid (0.45 g) in 4 ml of 0.5 M aqueous sodium hydroxide is added 1.8 g of ethylthiouroniumhydrobromide. The pH of the solution is adjusted to 9 with a solution of sodium hydroxide and maintained at that pH for 24 hours. The reaction mixture is then neutralized to a pH of 7 with hydrochloric acid and 2-acetylamino-2-difluoromethyl-5-guanidinopentanoic acid is isolated by ion exchange chromatography on an Amberlite IR 120 resin.

Workup

  1. temperaturemaintained at that pH for 24 hours

Sources & evidence

ORD record
ord-6913e961088d4df2bbe3663e31494f6a
Source dataset
uspto-grants-1985_01
Patent number
US04496588

Reaction notes

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