Cesium carbonate → Methyl 4-(N-(4-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoate

HRID 658606노트

반응식

HRID 658606 반응식
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]([CH2:7][NH:8][S:9]([C:12]2[CH:21]=[CH:20][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35]Br)=[CH:33][CH:32]=1>CC(C)=O>[F:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][N:8]([CH2:7][C:6]2[CH:22]=[CH:23][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[S:9]([C:12]2[CH:13]=[CH:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:20][CH:21]=2)(=[O:11])=[O:10])=[CH:33][CH:32]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 680214-Fluorobenzyl bromideHCID 26527056Methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate

생성물 1

HCID 57422334Methyl 4-(N-(4-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoate수율 65.2%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

Methyl 4-(N-(4-methoxybenzyl)sulfamoyl)benzoate (Example 5-10b) (4.3 g, 12.8 mmol) was dissolved in acetone (70 mL). Cesium carbonate (8.57 g, 25.6 mmol) and (4-fluorobenzyl bromide (1.76 mL, 14.08 mmol) were added and the mixture was stirred at room temperature overnight. The inorganic salts were filtered off and acetone was removed in vacuo. The residue was re-dissolved in ethyl acetate, washed with water and brine, then the organic layer was dried over magnesium sulfate and concentrated. The crude product was purified by re-crystallization with ethyl acetate/hexanes to afford pure Methyl 4-(N-(4-fluorobenzyl)-N-(4-methoxybenzyl)sulfamoyl)benzoate (3.7 g, 65%) as a white solid. 1H NMR (400 MHz, CDCl3): δ, ppm: 3.77 (s, 3H), 3.98 (s, 3H), 4.27 (s, 2H), 4.28 (s, 2H), 6.74 (d, 2H, J=8 Hz), 6.92 (m, 4H), 7.03 (m, 2H), 7.88 (d, 2H J=8 Hz), 8.16 (d, 2H, J=8 Hz).

후처리

  1. filtrationThe inorganic salts were filtered off
  2. customacetone was removed in vacuo
  3. dissolutionThe residue was re-dissolved in ethyl acetate
  4. washwashed with water and brine
  5. dry with materialthe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by re-crystallization with ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-9585903bad894615b0c064ae5b09095a
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08076491B2

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