4-Toluenesulfonyl chloride → Nalpha, Nepsilon-di-(4-methylbenzenesulfonyl)-L-lysine

HRID 1282503

Reaktionsgleichung

Reaktionsgleichung von HRID 1282503
Cl.Cl.[NH2:3][C@H:4]([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9].[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:15]=1>C1COCC1.C([O-])([O-])=O.[K+].[K+]>[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH:3][C@H:4]([C:10]([OH:12])=[O:11])[CH2:5][CH2:6][CH2:7][CH2:8][NH:9][S:20]([C:17]2[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=2)(=[O:22])=[O:21])(=[O:22])=[O:21])=[CH:16][CH:15]=1

Komponenten

5

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 69567Lysine dihydrochloride

Produkt 1

HCID 15696926Nalpha, Nepsilon-di-(4-methylbenzenesulfonyl)-L-lysineAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 11430Potassium CarbonateLösungsmittel

Versuchsvorschrift

To a stirred solution of L-lysine dihydrochloride (1 mmol) in a mixture of THF and 1M K2CO3 (3 mL/3 mL) was added 4-methylbenzenesulfonyl chloride (381 mg, 2.00 mmol). The reaction mixture was stirred for 2 h and then quenched with 1N HCl and extracted twice with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated. The crude was purified by flash chromatography using hexane/EtOAc/AcOH (30:69.4/0.6) to give 75% of the desired product.

Aufarbeitung

  1. customquenched with 1N HCl
  2. extractionextracted twice with EtOAc
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-915d743dfdb241378e7ba9e2653a7af0
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455587B1

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