Sodium Iodide → Methyl 2-((N-(2-methoxy-2-oxoethyl)-4-methylphenylsulfonamido)methyl)-4-phenoxybenzoate

HRID 1480929ノート

反応式

HRID 1480929 の反応式
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:17]Cl.[CH3:20][O:21][C:22](=[O:35])[CH2:23][NH:24][S:25]([C:28]1[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=1)(=[O:27])=[O:26].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:6][C:5]=1[CH2:17][N:24]([CH2:23][C:22]([O:21][CH3:20])=[O:35])[S:25]([C:28]1[CH:29]=[CH:30][C:31]([CH3:34])=[CH:32][CH:33]=1)(=[O:27])=[O:26]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 562880Methyl 2-(4-methylphenylsulfonamido)acetateHCID 86709143Methyl 2-(chloromethyl)-4-phenoxybenzoate

生成物 1

HCID 89812990Methyl 2-((N-(2-methoxy-2-oxoethyl)-4-methylphenylsulfonamido)methyl)-4-phenoxybenzoate収率 46.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a mixture of 2-chloromethyl-4-phenoxy-benzoic acid methyl ester (17.8 g, 64.3 mmol) in DMF (100 mL) was added (toluene-4-sulfonylamino)-acetic acid methyl ester (15.65 g, 64.3 mmol), K2CO3 (17.78 g, 128.6 mmol) and then NaI (964 mg, 6.43 mmol). The resulting mixture was stirred at 50° C. overnight. After cooled, reaction mixture was partitioned between EtOAc and water. The organic layer was washed with water (2×) and brine. It was dried over Na2SO4, filtered and concentrated. Crude residue was purified by silica gel chromatography to provide the title compound (14.34 g, 29.8 mmol). 1H NMR in CDCl3, δ in ppm: 7.86 (d, 1H, 8.8 Hz), 7.70 (d, 2H, J=8.4 Hz), 7.38-6.8 (m, 9H), 4.88 (s, 2H), 3.99 (s, 2H), 3.82 (s, 3H), 3.53 (s, 3H), 2.41 (s, 3H).

後処理

  1. temperatureAfter cooled
  2. customreaction mixture
  3. customwas partitioned between EtOAc and water
  4. washThe organic layer was washed with water (2×) and brine
  5. dry with materialIt was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customCrude residue was purified by silica gel chromatography

出典と根拠

ORDレコード
ord-5043ddbe29404d5f93e4066bcde605d1
出典データセット
uspto-grants-2016_08
特許番号
US09409892B2

反応ノート

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