Hydrochloric Acid → HCID 178512845, compound

HRID 1779852Notes

Reaction equation

HRID 1779852 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 2N 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 2N 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 2N sodium hydroxide to pH 7.5
  4. customdried by lyophilization

Sources & evidence

ORD record
ord-969fba161a894fb1a1f4f2d528f7c937
Source dataset
uspto-grants-1997_05
Patent number
US05629020

Reaction notes

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