Methyl iodide → Mglu1 C-11

HRID 2422719ノート

反応式

HRID 2422719 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 57404255Mglu1 C-11収率 33.4%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
45 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-5a259f87216b412b9ee86255024f0a4f
出典データセット
uspto-grants-2011_06
特許番号
US07960419B2

反応ノート

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