Glycine → Citraconic acid

HRID 1357316

Reaktionsgleichung

Reaktionsgleichung von HRID 1357316
[H][H].[S].NC[C:6]([OH:8])=[O:7].N[C@H:10]([C:18]([OH:20])=[O:19])[CH2:11][C:12]1C=NC=CC=1.N[C@H](C(O)=O)CS.[OH-].[Na+]>Cl>[CH3:12]/[C:11](=[CH:10]/[C:18]([OH:20])=[O:19])/[C:6]([OH:8])=[O:7]

Komponenten

7

Edukt 5

HCID 750GlycineHCID 14798Sodium HydroxideHCID 5362487SulfurHCID 131723969Pal cysteineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 643798Citraconic acidAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

With reference to Scheme 1, Br-DMMA is reacted with Pal-cysteine to afford a Pal-cysteine thiol ether of Formula III where R1 is hydrogen, R2 is methyl, R3 is palmityl (C15H31), X is sulfur, Y is a glycine radical (—NHCH(CO2H)—), n=1 and m=1. The reaction is carried out by adding Br-DMMA (0.3 g, 0.0014 mol) directly to a suspension of Pal-cysteine in 30 ml diluted HCl at room temperature. The pH of the mixture was gradually adjusted to 7, 9 and finally 11, using 1N NaOH. The pH of the mixture was stabilized after 2 h at pH 11. After 16 h stirring at 25° C., the mixture was filtered and the filtrate acidified using 1N HCl. A white precipitate occurred which was extracted with ether. Ether was evaporated under reduced pressure. The remaining greenish oil was dried under high vacuum. 3-S-(N-Palmityl cysteinyl) methyl, 2-methyl maleic acid (420 mg, 0.84 mmol) was obtained with a melting point of 60-63° C. Molar yield was 56%.

Aufarbeitung

  1. filtrationthe mixture was filtered
  2. extractionwas extracted with ether
  3. customEther was evaporated under reduced pressure
  4. customThe remaining greenish oil was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-7992e1cda16947f5bc22ef91d2728929
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06590071B1

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