Reaction equation
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]=1Participants
5
Procedure
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).
Workup
- customWallbank, Synthesis 1103 (1987) (incorporated by reference)
- filtrationThe next day, the reaction mixture is filtered
- concentrationthe filtrate is concentrated in vacuo
- customThe crude residue is purified by flash chromatography (silica gel, 10% ethyl acetate/hexane)
Sources & evidence
- ORD record
- ord-362f2eddf77345ecbc575afc59333e25
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07122579B2
Linked notes
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