7-Aminocephalosporanic acid → 3-[(2-Methyl-1,3,4-thiadiazol-5-yl-thio)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 2398966

反応式

HRID 2398966 の反応式
ClCC1C=CC([CH:9]([C:13](O)=O)C(O)=O)=CC=1.CC(OC[C:21]1CS[C@@H:24]2[C@H:25](N)C(=O)[N:23]2[C:22]=1C(O)=O)=O.[CH3:34][C:35]1[S:36][C:37]([S:40][CH2:41][C:42]2[CH2:49][S:48][CH:47]3[N:44]([C:45](=[O:51])[CH:46]3[NH2:50])[C:43]=2[C:52]([OH:54])=[O:53])=[N:38][N:39]=1>C(Cl)Cl.C(O)CC>[CH2:22]([NH+:23]([CH2:9][CH3:13])[CH2:24][CH3:25])[CH3:21].[CH3:34][C:35]1[S:36][C:37]([S:40][CH2:41][C:42]2[CH2:49][S:48][CH:47]3[N:44]([C:45](=[O:51])[CH:46]3[NH2:50])[C:43]=2[C:52]([O-:54])=[O:53])=[N:38][N:39]=1.[CH3:34][C:35]1[S:36][C:37]([S:40][CH2:41][C:42]2[CH2:49][S:48][CH:47]3[N:44]([C:45](=[O:51])[CH2:46]3)[C:43]=2[C:52]([OH:54])=[O:53])=[N:38][N:39]=1

参加物

7

反応物 3

HCID 4413287-Aminocephalosporanic acidHCID 31498227-Amino-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 22767749p-Chloromethylphenylmalonic acid

生成物 2

HCID 214366563-[(2-Methyl-1,3,4-thiadiazol-5-yl-thio)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidHCID 1317108003-[(2-Methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid triethylammonium salt

試薬・触媒・溶媒 2

HCID 10311-Propanol溶媒HCID 6344Dichloromethane溶媒

実験手順

α-Carboxy-p-chloromethylphenylacetylnitrophenyl polymer, prepared according to the procedure described in Canadian Pat. No. 892,580, carrying 4m. mole of p-chloromethylphenylmalonic acid is suspended for about 8 hours in 20 ml of dry methylene chloride solution containing 1 m. mole of 3-[(2-methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid triethylammonium salt, which is prepared from the 7-aminocephalosporanic acid derivative and triethylamineat room temperature. After only traces of 3-[(2-methyl-1,3,4-thiadiazol-5-ylthio)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid remain in solution, which is determined by thin layer chromatography on cellulose in 70% aqueous propanol, the polymer is filtered off and washed with three portions of 50ml each of methylene chloride. The combined filtrates are evaporated and the residue is dissolved in 20 ml of distilled water. This solution is acidified to pH 2 by adding 0.2 N hydrochloric acid and extracted twice with ethylacetate. The organic solution is dried over sodium sulfate and evaporated to room temperature. The remaining solid is dried overnight over phosphorus pentoxide under vacuum to give 7-[[2-[4-chloromethyl)phenyl]-2-carboxyacetyl]amino]-3-[(2-methyl-1,3,4-thiadiazol-5-yl-thio)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid.

後処理

  1. customα-Carboxy-p-chloromethylphenylacetylnitrophenyl polymer, prepared
  2. additioncontaining 1 m
  3. filtrationthe polymer is filtered off
  4. washwashed with three portions of 50ml each of methylene chloride
  5. customThe combined filtrates are evaporated
  6. dissolutionthe residue is dissolved in 20 ml of distilled water
  7. additionby adding 0.2 N hydrochloric acid
  8. extractionextracted twice with ethylacetate
  9. dry with materialThe organic solution is dried over sodium sulfate
  10. customevaporated to room temperature
  11. dry with materialThe remaining solid is dried overnight over phosphorus pentoxide under vacuum

出典と根拠

ORDレコード
ord-3e5418ba462f4fc6aa5a7ff88d7d8141
出典データセット
uspto-grants-1977_05
特許番号
US04026887

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