Hydrochloric Acid → N-cyclohexanoyl-(L)-citrulline

HRID 1779851Notes

Reaction equation

HRID 1779851 reaction equation
[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7]([NH2:9])=[O: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]([NH2:9])=[O:8])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 9750CitrullineHCID 75938Cyclohexanecarbonyl chloride

Product 1

HCID 10613142N-cyclohexanoyl-(L)-citrullineYield 77.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

L-Citrulline (35.2 g., 0.2 mole) was dissolved in 200 mL of 2N sodium hydroxide. Cyclohexanoyl chloride (29 mL, 0.2 mole) was added dropwise to the mixture. The reaction mixture was maintained at about 25° C. for 1 hour. The mixture was then acidified to pH 2.6 with aqueous (4:1) hydrochloric acid. The precipitate which formed was separated by decantation. The solids were dissolved in 2N sodium hydroxide to pH 6.5 and dried by lyophilization to furnish 44.2 g of N-cyclohexanoyl-(L)-citrulline. The product was a white solid.

Workup

  1. customThe precipitate which formed
  2. customwas separated by decantation
  3. dissolutionThe solids were dissolved in 2N sodium hydroxide to pH 6.5
  4. customdried by lyophilization

Sources & evidence

ORD record
ord-35e6658cdc9f4c519114263f870d8582
Source dataset
uspto-grants-1997_05
Patent number
US05629020

Reaction notes

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