Hydrochloric Acid → HCID 178512847, compound

HRID 397249Notes

Reaction equation

HRID 397249 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[CH:13]1([C:19](Cl)=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.Cl>[OH-].[Na+]>[CH:13]1([C:19]([NH:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 75938Cyclohexanecarbonyl chlorideHCID 178418600HCID 178418600, compound

Product 1

HCID 178512847HCID 178512847, compoundYield 37.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

(L)-Arginine (103.2 g., 0.6 mole) was dissolved in 600 mL of 2 N sodium hydroxide. Cyclohexanoyl chloride (87 mL, 0.6 mole) was added dropwise to the mixture. The reaction mixture was maintained at 50° C. for 2 hours. The mixture was then cooled to room temperature and acidified to pH 2.3 with aqueous (4:1) hydrochloric acid. The precipitate which formed was separated by decantation. The solids were dissolved in 2 N sodium hydroxide and dried by lyophilization to furnish 64.1 g of crude N-cyclohexanoyl-(L)-arginine. The product was purified by column chromatography on silica gel/using butanol/acetic acid/water as the eluent system. The products isolated were N-cyclohexanoyl-(L)-arginine and Nα,Nγ-dicyclohexanoyl-(L)-arginine.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. customThe precipitate which formed
  3. customwas separated by decantation
  4. dissolutionThe solids were dissolved in 2 N sodium hydroxide
  5. customdried by lyophilization

Sources & evidence

ORD record
ord-d0e13ed49d004e43a3578ace99baa054
Source dataset
uspto-grants-2003_08
Patent number
US06610329B2

Reaction notes

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