Methanol → L-Thyronine

HRID 1386964

Reaktionsgleichung

Reaktionsgleichung von HRID 1386964
C[O:2][C:3](=[O:22])[C@H:4]([CH2:12][C:13]1[CH:18]=[C:17](I)[C:16]([OH:20])=[C:15](I)[CH:14]=1)[NH:5]C(=O)C(F)(F)F.[IH2+].N12[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[CH2:29]CCCN2.C[OH:36]>>[NH2:5][C@H:4]([C:3]([OH:2])=[O:22])[CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:20][C:33]2[CH:34]=[CH:29][C:30]([OH:36])=[CH:31][CH:32]=2)=[CH:17][CH:18]=1

Komponenten

5

Edukt 4

HCID 887MethanolHCID 3715291Iodine, ion (I1+)HCID 13941953N-Trifluoroacetyl-3,5-diiodotyrosine methyl esterHCID 21921200Diazabicyclo[5.4.0]undecane

Produkt 1

HCID 5461103L-ThyronineAusbeute 4 %

Versuchsvorschrift

N-Trifluoroacetyl-3,5-diiodotyrosine methyl ester (552 mg, 1.0 mmol) prepared according to the procedure of N. Lewis and P. Wallbank, Synthesis 1103 (1987) (incorporated by reference) and all of the crude iodonium salt (3) from above is dissolved in 5 mL of anhydrous methanol. Diazabicyclo[5.4.0]undecane (DBU) (183 mg, 1.2 mmol) and a spatula tip of copper-bronze are added and the resulting mixture is stirred at room temperature overnight. The next day, the reaction mixture is filtered, and the filtrate is concentrated in vacuo. The crude residue is purified by flash chromatography (silica gel, 10% ethyl acetate/hexane) to provide 30 mg (4%) of the protected thyronine adduct (4).

Aufarbeitung

  1. customWallbank, Synthesis 1103 (1987) (incorporated by reference)
  2. filtrationThe next day, the reaction mixture is filtered
  3. concentrationthe filtrate is concentrated in vacuo
  4. customThe crude residue is purified by flash chromatography (silica gel, 10% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-48633e4e0fe043db91c7e0a8ebab2b42
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06266622B1

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