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

HRID 397250

Reaction equation

HRID 397250 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 2 N 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 2 N 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 2 N sodium hydroxide to pH 6.5
  4. customdried by lyophilization

Sources & evidence

ORD record
ord-de78eb22f496417d8be36aebed0b2ccf
Source dataset
uspto-grants-2003_08
Patent number
US06610329B2

Linked notes

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