Ethanol → ethyl Nalpha-benzyloxycarbonyl-L-lysinate

HRID 979176

Reaktionsgleichung

Reaktionsgleichung von HRID 979176
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([OH:20])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21](O)[CH3:22].S(=O)(=O)(O)O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 11430Potassium CarbonateHCID 75172N-alpha-Benzyloxycarbonyl-L-lysine

Produkt 1

HCID 13851264ethyl Nalpha-benzyloxycarbonyl-L-lysinateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture containing 29.9 gm (0.017 mol) of Nα-benzyloxycarbonyl-L-lysine, 30 ml of ethanol, and 9.0 ml of concentrated sulfuric acid in 250 ml of methylene chloride was refluxed for 22.5 hours. The reaction mixture was then cooled to room temperature and basified to pH of about 13 by the careful addition of a saturated aqueous solution of potassium carbonate. The aqueous phase was removed and the organic phase was washed one more time with a saturated potassium carbonate solution. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo to give 29.8 gm (91% ) of ethyl Nα-benzyloxycarbonyl-L-lysinate (II-F) as an oil.

Aufarbeitung

  1. temperaturewas refluxed for 22.5 hours
  2. customThe aqueous phase was removed
  3. washthe organic phase was washed one more time with a saturated potassium carbonate solution
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c7dcab290ba14e1698ae447fcf7f853b
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04666906

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