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Phosphoric Acid → 7-Acetoacetamido-3-(5-methyl-1,3,4-oxadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 596793
ノート
印刷プレビュー

反応式

HRID 596793 の反応式
[C:1]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15]OC(=O)C)[CH2:13][S:14][C@H:9]12)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(=O)([O-])O.[Na+].[CH3:30][C:31]1[O:35][C:34]([SH:36])=[N:33][N:32]=1.P([O-])([O-])([O-])=O.P(=O)(O)(O)O>O.C(OCC)(=O)C>[C:1]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15][S:36][C:34]3[O:35][C:31]([CH3:30])=[N:32][N:33]=3)[CH2:13][S:14][C@H:9]12)(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 1004Phosphoric AcidHCID 1061PhosphateHCID 516892Sodium BicarbonateHCID 887151507-Acetoacetamido-3-acetoxymethyl-3-cephem-4-carboxylic acidHCID 178434159HCID 178434159、化合物

生成物 1

HCID 1317106647-Acetoacetamido-3-(5-methyl-1,3,4-oxadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid
収率 48%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 0.178 g. of 7-acetoacetamido-3-acetoxymethyl-3-cephem-4-carboxylic acid, 0.42 g. of sodium hydrogen carbonate, 0.64 g. of 5-methyl-1,3,4-oxadiazole-2-thiol and 10 ml. of a phosphate buffer of pH 6.4 is heated at 55°-60° C for 16 hours. After cooling, the reaction mixture is shaken with ethyl acetate and the water layer is taken, adjusted to pH 2 with 50 % phosphoric acid and extracted three times with ethyl acetate. The extracts are pooled, washed with water and dehydrated over sodium sulfate. Then, the solvent is distilled off and ether is added to the residue, whereupon 0.10 g. (48 %) of 7-acetoacetamido-3-(5-methyl-1,3,4-oxadiazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid is obtained as crystals melting at 80°-85° C(decomp.).

後処理

  1. additionA mixture of 0.178 g
  2. temperatureAfter cooling
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water
  5. distillationThen, the solvent is distilled off
  6. additionether is added to the residue, whereupon 0.10 g

出典と根拠

ORDレコード
ord-4d48a21fcf174b318f54198c022910f4
出典データセット
uspto-grants-1977_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04012379

反応ノート

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