Acetone → {[2-(7-Methoxy-benzo[1,3]dioxole-5-carbonyl)-benzenesulfonyl]-o-tolyl-amino}-acetic acid methyl ester

HRID 1265333

反応式

HRID 1265333 の反応式
CC(C)=O.[CH3:5][O:6][C:7](=[O:39])[CH2:8][N:9]([S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[CH:26]([OH:38])[C:27]1[CH:35]=[C:34]([O:36][CH3:37])[C:30]2[O:31][CH2:32][O:33][C:29]=2[CH:28]=1)(=[O:19])=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>C(OCC)(=O)C>[CH3:5][O:6][C:7](=[O:39])[CH2:8][N:9]([S:17]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]([C:27]1[CH:35]=[C:34]([O:36][CH3:37])[C:30]2[O:31][CH2:32][O:33][C:29]=2[CH:28]=1)=[O:38])(=[O:18])=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16]

参加物

6

反応物 4

HCID 180AcetoneHCID 3776IsopropanolHCID 22965597({2-[Hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-benzenesulfonyl}-o-tolyl-amino)-acetic acid methyl esterHCID 131709961Jones' reagent

生成物 1

HCID 22965596{[2-(7-Methoxy-benzo[1,3]dioxole-5-carbonyl)-benzenesulfonyl]-o-tolyl-amino}-acetic acid methyl ester収率 59%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To acetone (225 mL) was added ({2-[hydroxy-(7-methoxy-benzo[1,3]dioxol-5-yl)-methyl]-benzenesulfonyl}-o-tolyl-amino)-acetic acid methyl ester (4.17 g, 8.35 mmol), and 8N Jones reagent (4 mL). The mixture was stirred 15 minutes giving a suspended solid. Isopropanol (20 mL) was added followed by stirring for 15 minutes. The mixture was filtered, saturated sodium bicarbonate solution was added, and the solvent was removed in vacuo giving a paste. The paste was resuspended in ethyl acetate and water, filtered, and washed with saturated sodium bicarbonate, brine and dried over anhydrous magnesium sulfate. The solution was filtered and evaporated to a solid which was crystallized from ethyl acetate and ethyl ether giving a white solid, 2.41 g, 59% yield, mp 159-170° C. NMR spectra and elemental analysis were consistent with the structure.

後処理

  1. customgiving a suspended solid
  2. stirringby stirring for 15 minutes
  3. filtrationThe mixture was filtered
  4. additionsaturated sodium bicarbonate solution was added
  5. customthe solvent was removed in vacuo
  6. customgiving a paste
  7. filtrationwater, filtered
  8. washwashed with saturated sodium bicarbonate, brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThe solution was filtered
  11. customevaporated to a solid which
  12. customwas crystallized from ethyl acetate and ethyl ether giving a white solid, 2.41 g, 59% yield, mp 159-170° C

出典と根拠

ORDレコード
ord-0a19bab66980475f8dcb50a5fcef95bc
出典データセット
uspto-grants-2003_04
特許番号
US06545150B2

関連ノート

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