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

HRID 567633

Reaktionsgleichung

Reaktionsgleichung von HRID 567633
[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

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 9750CitrullineHCID 75938Cyclohexanecarbonyl chloride

Produkt 1

HCID 10613142N-cyclohexanoyl-(L)-citrullineAusbeute 77,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-2d03e23fadaf4b0b89c76bd3cf88f2ec
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06180140B2

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