Sodium Bicarbonate → Ethyl N-(tert-butoxycarbonyl)-L-tyrosinate

HRID 253735

Reaktionsgleichung

Reaktionsgleichung von HRID 253735
Cl.[CH2:2]([O:4][C:5](=[O:16])[C@H:6]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[NH2:7])[CH3:3].[C:17]([O-:20])(O)=[O:18].[Na+]>C(Cl)Cl.O.CCOC(C)=O>[CH2:2]([O:4][C:5](=[O:16])[C@H:6]([CH2:8][C:9]1[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=1)[NH:7][C:17]([O:20][C:9]([CH3:14])([CH3:10])[CH3:8])=[O:18])[CH3:3]

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 2724939Tyrosine ethyl ester hydrochloride

Produkt 1

HCID 11077750Ethyl N-(tert-butoxycarbonyl)-L-tyrosinateAusbeute 180,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 21908982Water methylene chlorideLösungsmittel

Versuchsvorschrift

To a mixture of L-tyrosine ethyl ester hydrochloride (55.08 g) and NaHCO3 (22.52 g) in CH2Cl2/H2O (280 ml/280 ml) was added di-tert-butyl bicarbonate (56.82 g) portionwise. The mixture was stirred for 2 hours at room temperature and diluted with AcOEt. The organic layer was washed with H2O, dried (Na2SO4) and evaporated. The residue was recrystallized from a mixture of diethyl ether and hexane to yield N-(tert-butoxycarbonyl)-L-tyrosine ethyl ester (62.71 g). mp. 87-88° C.; MS(APCI) m/z 327(M+NH4), 310(M+H).

Aufarbeitung

  1. washThe organic layer was washed with H2O
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was recrystallized from a mixture of diethyl ether and hexane

Quellen und Nachweise

ORD-Eintrag
ord-c8274991ad464f84a60a0d3856d7848e
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872151B2

Verknüpfte Notizen

Wird geladen…