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

HRID 1480929노트

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HRID 1480929 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5043ddbe29404d5f93e4066bcde605d1
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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