2-Naphthalenesulfonyl chloride → N-(2-naphthylsulfonyl)-glycine t-butyl ester

HRID 1734315

Reaktionsgleichung

Reaktionsgleichung von HRID 1734315
C(N(CC)CC)C.Cl.[C:9]([O:13][C:14](=[O:17])[CH2:15][NH2:16])([CH3:12])([CH3:11])[CH3:10].[CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][C:19]=1[S:28](Cl)(=[O:30])=[O:29]>C(Cl)Cl.CCOCC>[C:9]([O:13][C:14](=[O:17])[CH2:15][NH:16][S:28]([C:19]1[CH:20]=[CH:21][C:22]2[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=1)(=[O:30])=[O:29])([CH3:12])([CH3:11])[CH3:10]

Komponenten

6

Edukt 3

HCID 71252-Naphthalenesulfonyl chlorideHCID 8471TriethylamineHCID 2725036Glycine tert-butyl ester hydrochloride

Produkt 1

HCID 19081114N-(2-naphthylsulfonyl)-glycine t-butyl esterAusbeute 87,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

14.4 ml of triethylamine are added dropwise to 6.91 g of glycine t-butyl ester hydrochloride and 12.1 g of 2-naphthylsulfonyl chloride in 70 ml of methylene chloride. The reaction mixture is subsequently diluted with 200 ml of ether. The organic phase is washed with 1N hydrochloric acid and with water. After drying and evaporation the residue is suspended in ether and suction filtered. After drying the crystals there are obtained 11.57 g of N-(2-naphthylsulfonyl)-glycine t-butyl ester, Rf=0.49 (ether/hexane 2:1).

Aufarbeitung

  1. washThe organic phase is washed with 1N hydrochloric acid and with water
  2. customAfter drying
  3. customevaporation the residue
  4. filtrationsuction filtered
  5. customAfter drying the crystals

Quellen und Nachweise

ORD-Eintrag
ord-bdcba9e062f14c179d655704a4886566
Quelldatensatz
uspto-grants-1996_07
Patentnummer
US05532232

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