Methyl iodide → Mglu1 C-11

HRID 2422719

Reaktionsgleichung

Reaktionsgleichung von HRID 2422719
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[C:11]([NH:14][C:15]([C@@H:17]3[CH2:19][C@H:18]3[CH3:20])=[O:16])[S:10][N:9]=2)=[CH:4][CH:3]=1.[C:21]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH3:21][O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH3:13])=[C:11]([NH:14][C:15]([C@@H:17]3[CH2:19][C@H:18]3[CH3:20])=[O:16])[S:10][N:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 136244237(R,R)-N-[3-(4-hydroxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide

Produkt 1

HCID 57404255Mglu1 C-11Ausbeute 33,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a dry flask containing (R,R)—N-[3-(4-hydroxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide (100 mg, 0.347 mmol) is added dry acetone (2 mL), K2CO3 (50 mg, 0.347 mmol), and methyl iodide (19 μL, 0.313 mmol). The reaction mixture is heated 16 h at 45° C. and treated with additional methyl iodide (19 μL, 0.313 mmol). After heating for another 6 h, the solvent is evaporated, and the residue is partitioned between ethyl acetate and water. The ethyl acetate solution is washed (satd aqueous K2CO3 (twice) and brine), dried (MgSO4), and the solvent evaporated. Chromatography over silica gel, eluting with EtOAc/hexanes, affords (R,R)—N-[3-(4-methoxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropane-carboxamide (35 mg, 33%) as a white solid. 1H NMR; ES-MS: m/e 303 (m+1).

Aufarbeitung

  1. temperatureAfter heating for another 6 h
  2. customthe solvent is evaporated
  3. customthe residue is partitioned between ethyl acetate and water
  4. washThe ethyl acetate solution is washed (
  5. dry with materialdried (MgSO4)
  6. customthe solvent evaporated
  7. washChromatography over silica gel, eluting with EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5a259f87216b412b9ee86255024f0a4f
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07960419B2

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