Water → 2,4,6-Trimethylbenzenesulfonic acid

HRID 65520ノート

反応式

HRID 65520 の反応式
O.O.O.[C:4]1([CH3:16])[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[S:12]([OH:15])(=[O:14])=[O:13]>C(Cl)Cl.C(OCC)(=O)C>[C:4]1([CH3:16])[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([CH3:11])[C:5]=1[S:12]([OH:15])(=[O:14])=[O:13]

参加物

5

反応物 2

HCID 962WaterHCID 156203442-Mesitylenesulfonic acid dihydrate

生成物 1

HCID 769922,4,6-Trimethylbenzenesulfonic acid収率 352.5%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

In 50 ml of anhydrous methylene chloride was suspended 6.94 g of 2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminothioacetic acid-S-methyl ester, and 4.26 g of boron trifluoride-diethyl ether complex was added with ice-cooling to the resulting suspension to form a solution. Then, 40 ml of an anhydrous methylene chloride solution containing 4.10 g of pivaloyloxymethyl 7-amino-3-[2-(5-methyl-1,2,3,4-tetrazolyl)]methyl-Δ3 -cephem-4-carboxylate was added to the solution, and the resulting mixture was subjected to reaction at room temperature for 7 hours. The reaction mixture obtained was introduced into 50 ml of water, and the organic layer was separated. Then, 50 ml of water was added to the organic layer, and the pH was adjusted to 0.5 with 6N hydrochloric acid. Then, the organic layer was separated, and 50 ml of water was added thereto. The pH was adjusted to 5.0 with sodium hydrogencarbonate. The organic layer was further separated, washed with 50 ml of saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. After removing the solvent by distillation under reduced pressure, the residue obtained was dissolved in 80 ml of ethyl acetate. Then, 2.36 g of mesitylenesulfonic acid dihydrate was added to the resulting solution, and stirred for 30 minutes, and the precipitated crystals were collected by filtration to obtain 7.05 g (yield, 88.8%) of mesitylenesulfonic acid salt of pivaloyloxymethyl 7-[2-(2-aminothiazol-4-yl)-2-(syn)-methoxyiminoacetamido]-3-[2-(5-methyl-1,2,3,4-tetrazolyl)]methyl-Δ3 -cephem-4-carboxylate having a melting point of 218°-220° C. (decomp.).

後処理

  1. additionwas added with ice-
  2. temperaturecooling to the resulting suspension
  3. customto form a solution
  4. additionwas added to the solution
  5. customthe resulting mixture was subjected to reaction at room temperature for 7 hours
  6. customThe reaction mixture obtained
  7. customthe organic layer was separated
  8. additionThen, 50 ml of water was added to the organic layer
  9. customThen, the organic layer was separated
  10. addition50 ml of water was added
  11. washwashed with 50 ml of saturated aqueous sodium chloride solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. customAfter removing the solvent
  14. distillationby distillation under reduced pressure
  15. customthe residue obtained
  16. filtrationthe precipitated crystals were collected by filtration

出典と根拠

ORDレコード
ord-f17ff74ff65c4835ac6ff4d0ff992226
出典データセット
uspto-grants-1986_09
特許番号
US04614819

反応ノート

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