Methyl iodide → Mglu1 C-11

HRID 2422719

반응식

HRID 2422719 반응식
[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

참가 물질

5

반응물 3

HCID 6328Methyl iodide2회HCID 11430Potassium CarbonateHCID 136244237(R,R)-N-[3-(4-hydroxyphenyl)-4-methylisothiazol-5-yl]-2-methylcyclopropanecarboxamide

생성물 1

HCID 57404255Mglu1 C-11수율 33.4%

시약·촉매·용매 1

HCID 180Acetone용매

반응 조건

온도
45 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5a259f87216b412b9ee86255024f0a4f
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960419B2

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