D-Tyrosine → o-Benzyl-D-tyrosine

HRID 1646914

Reaktionsgleichung

Reaktionsgleichung von HRID 1646914
[NH2:1][C@@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:1][C@@H:2]([C:11]([OH:13])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:10][CH2:3][C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH:8][CH:9]=1

Komponenten

3

Edukt 1

HCID 71098D-Tyrosine2×

Produkt 1

HCID 725704o-Benzyl-D-tyrosine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

7,5 g of a chloromethylated styrene-divinylbenzene copolymer (Merrifield resin, 1% cross-linked) are esterified with 1.113 g of Boc-D-Tyr(Bzl)-OH (3 mmoles) by refluxing for 45 hours in 60 ml of ethyl acetate in the presence of 0.42 ml of triethylamine. The resin is separated by filtration, washed successively with ethyl acetate, ethanol and water, and dried under vacuum at 25° C. 8.09 g of Boc-D-Tyr(Bzl)-resin are obtained having an esterification degree of 0.201 mmoles of D-Tyr/g calculated on the basis of the difference between the total amount of D-Tyr derivative employed and the one remained in mother liquors and in washings (determination by UV at 276 nm). The resin is Boc-deprotected by treatment with 70 ml of TFA/CH2Cl2 1/1 for 30 minutes at room temperature; thereafter it is filtered and suspended for 30 minutes under stirring in 70 ml of 10% triethylamine in chloroform. After filtrating, washing with chloroform and drying under vacuum, the product H-D-Tyr(Bzl)-resin is obtained.

Aufarbeitung

  1. customfor 30 minutes
  2. customat room temperature
  3. filtrationthereafter it is filtered
  4. filtrationAfter filtrating
  5. washwashing with chloroform
  6. customdrying under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3be09a456f544d0b861e0ac2a351b59a
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05182265

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