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Ethyl cysteinate hydrochloride → S-[2-(1-benzyloxycarbonyl-4-piperidyl)ethyl]-L-cysteine ethyl ester

HRID 1638989
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1638989
Cl.[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][SH:9])[NH2:7])[CH3:3].[O-]CC.[Na+].[Na].[CH2:16]([O:23][C:24]([N:26]1[CH2:31][CH2:30][CH:29]([CH2:32][CH2:33]I)[CH2:28][CH2:27]1)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C(O)C>[CH2:2]([O:4][C:5](=[O:10])[C@H:6]([CH2:8][S:9][CH2:33][CH2:32][CH:29]1[CH2:28][CH2:27][N:26]([C:24]([O:23][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[O:25])[CH2:31][CH2:30]1)[NH2:7])[CH3:3]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 2723617Ethyl cysteinate hydrochlorideHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 14600697Benzyl 4-(2-iodoethyl)piperidine-1-carboxylate

Produkt 1

HCID 14600711S-[2-(1-benzyloxycarbonyl-4-piperidyl)ethyl]-L-cysteine ethyl esterAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel
2×

Versuchsvorschrift

In a nitrogen gas flow, 8.3 g of L-cysteine ethyl ester hydrochloride is added to a sodium ethoxide solution prepared by adding 2 g of metallic sodium to 80 ml of absolute ethanol. After stirring for 1 hours at room temperature, 80 ml of an ethanol solution containing 18.4 g of 2-(1-benzyloxycarbonyl-4-piperidyl)ethyl iodide is added dropwise to this reaction mixture. After stirring for 1 hour at room temperature, the reaction liquid is concentrated under reduced pressure. To the resulting residue, ice-cold water is added. After extracting with ether, the organic layer is washed with water, and dried over magnesium sulfate. Thereafter, the solvent is distilled off under reduced pressure to give 16.3 g of oily S-[2-(1-benzyloxycarbonyl-4-piperidyl)ethyl]-L-cysteine ethyl ester.

Aufarbeitung

  1. customprepared
  2. additionis added dropwise to this reaction mixture
  3. stirringAfter stirring for 1 hour at room temperature
  4. customthe reaction liquid
  5. concentrationis concentrated under reduced pressure
  6. additionTo the resulting residue, ice-cold water is added
  7. extractionAfter extracting with ether
  8. washthe organic layer is washed with water
  9. dry with materialdried over magnesium sulfate
  10. distillationThereafter, the solvent is distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-c92e75a3332149228b45d799ac941ab9
Quelldatensatz
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04882326

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