Methanol → L-Thyronine

HRID 1244684

반응식

HRID 1244684 반응식
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

참가 물질

5

반응물 4

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

생성물 1

HCID 5461103L-Thyronine수율 4%

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-362f2eddf77345ecbc575afc59333e25
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07122579B2

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