Hydrochloric Acid → HCID 178512847, compound

HRID 726453Notes

Reaction equation

HRID 726453 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 2N 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 2N 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 N(α)-N(ε)-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 2N sodium hydroxide
  5. customdried by lyophilization

Sources & evidence

ORD record
ord-ffed4e1535b146e3bd10ca2d641507c0
Source dataset
uspto-grants-1998_01
Patent number
US05709861

Reaction notes

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