Hydrochloric Acid → HCID 178512845, compound

HRID 1584698Notes

Reaction equation

HRID 1584698 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:18](Cl)=[O:19])[CH2:17][CH2:16][CH2:15][CH2:14]1.Cl>[OH-].[Na+]>[CH:13]1([C:18]([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:19])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 78284Cyclopentanecarbonyl chlorideHCID 178418600HCID 178418600, compound

Product 1

HCID 178512845HCID 178512845, compoundYield 131.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

(L)-Arginine (32.8 g., 0.19 moles) was dissolved in 188 mL of 2 N sodium hydroxide. Cyclopentanoyl chloride (22.9 mL, 0.19 moles) were added dropwise to the mixture. The reaction mixture was maintained at about 25° C. for 2 hours. The mixture was then acidified to pH 1.5 with aqueous (4:1) hydrochloric acid. The precipitate which formed was separated by decantation. The solids were dissolved in 2 N sodium hydroxide to pH 7.5 and dried by lyophilization to furnish 67.4 g of N-cyclopentanoyl-(L)-arginine. The product was a white solid. Mass Spectrum: M+1 m/e 271.

Workup

  1. customThe precipitate which formed
  2. customwas separated by decantation
  3. dissolutionThe solids were dissolved in 2 N sodium hydroxide to pH 7.5
  4. customdried by lyophilization

Sources & evidence

ORD record
ord-462772fad34c400d931786e1a127fc3b
Source dataset
uspto-grants-1999_08
Patent number
US05935601

Reaction notes

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