反応式
CON(C)[C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH2:17][O:18][CH3:19])=[O:5].[CH3:21][Mg]Br.C1(C)C=CC=CC=1.C1COCC1>C1COCC1>[CH3:19][O:18][CH2:17][C:7]1[N:8]=[C:9]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[S:10][C:6]=1[C:4](=[O:5])[CH3:21]参加物
実験手順
To a solution of the above-prepared 4-methoxymethyl-2-phenyl-thiazole-5-carboxylic acid methoxy-methyl amide (6.706 g, 22.9 mmole, 1.0 eq) in dry THF (25 ml) at 0° C. was added dropwise a solution of 1.4M methylmagnesium bromide in (3:1)toluene-THF (32.7 ml, 45.8 mmole, 2.0 eq). The resulting tan suspension was stirred under nitrogen at room temperature for 30 minutes, then quenched by the addition of saturated ammonium chloride and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give a brown oil. Silica gel chromatography using a gradient elution of (9:1) to (4:1) hexanes-ethyl acetate provided the title compound (6.033 g, 81%) as a yellow crystalline solid. 1H NMR (CDCl3): δ 2.7 (s, 3H), 3.5 (s, 3H), 4.9 (s, 2H) 7.4-7.5 (m, 3H), 8.0 (m, 2H).
後処理
- customquenched by the addition of saturated ammonium chloride
- extractionextracted with ethyl acetate
- washThe organic phase was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customto give a brown oil
- washa gradient elution of (9:1) to (4:1) hexanes-ethyl acetate
出典と根拠
- ORDレコード
- ord-8de9488206cc44e58d5fa5c2a2061221
- 出典データセット
- uspto-grants-2003_08
- 特許番号
- US06608087B1
関連ノート
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