Hydrochloric Acid → 3-Methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acid

HRID 1979784ノート

反応式

HRID 1979784 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:27])[CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15](=[O:28])[N:10]2[C:11]=1[C:12]([O-:14])=[O:13])(=O)C.[Na+].[Cl-].[Ca+2].[Cl-].Cl>CO>[CH3:1][O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18](=[O:27])[CH2:19][O:20][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:15](=[O:28])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 5284359Calcium ChlorideHCID 23673564Sodium 3-acetoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate

生成物 1

HCID 159176843-Methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acid収率 80.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

10 g of sodium 3-acetoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylate were dissolved in 100 ml of a 67% v/v aqueous methanol solution. 100 g of anhydrous calcium chloride were added to the solution, and then the mixture was stirred at 70° C. for 45 minutes. At the end of this time, 100 ml of ice-water, followed by 10 ml of 1N hydrochloric acid, were added to the reaction mixture. The reaction mixture was then extracted three times, each time with 100 ml of ethyl acetate. The extracts were combined, washed with an aqueous solution of sodium chloride and then extracted with two 50 ml portions of a 10% w/v aqueous solution of dipotassium phosphate. The extracts were combined, washed with a small amount of ethyl acetate and then acidified by the addition of a saturated aqueous solution of potassium hydrogen sulphate. The mixture was then extracted twice, each time with 100 ml of ethyl acetate. The ethyl acetate extracts were combined, washed with an aqueous solution of sodium chloride, dehydrated by the addition of anhydrous magnesium sulphate and then concentrated by evaporation under reduced pressure, to give 7.15 g of 3-methoxymethyl-7-phenoxyacetamido-3-cephem-4-carboxylic acid, in the form of a yellow solid.

後処理

  1. additionwere added to the reaction mixture
  2. extractionThe reaction mixture was then extracted three times
  3. washwashed with an aqueous solution of sodium chloride
  4. extractionextracted with two 50 ml portions of a 10% w/v aqueous solution of dipotassium phosphate
  5. washwashed with a small amount of ethyl acetate
  6. additionacidified by the addition of a saturated aqueous solution of potassium hydrogen sulphate
  7. extractionThe mixture was then extracted twice
  8. washwashed with an aqueous solution of sodium chloride
  9. additiondehydrated by the addition of anhydrous magnesium sulphate
  10. concentrationconcentrated by evaporation under reduced pressure

出典と根拠

ORDレコード
ord-33fd2f9dca0e45dcad8a2198f83f9a5b
出典データセット
uspto-grants-1984_11
特許番号
US04482710

反応ノート

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