Sodium Carbonate → 7-[2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

HRID 261647

反応式

HRID 261647 の反応式
P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][O:8][N:9]=[C:10]([C:14]1[N:15]=[C:16]([NH2:19])[S:17][CH:18]=1)[C:11]([OH:13])=O.[NH2:20][CH:21]1[C:39](=[O:40])[N:23]2[C:24]([C:36]([OH:38])=[O:37])=[C:25]([CH2:28][S:29][C:30]3[N:34]([CH3:35])[N:33]=[N:32][N:31]=3)[CH2:26][S:27][C@H:22]12.C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl.CC(C)=O>[CH3:7][O:8][N:9]=[C:10]([C:14]1[N:15]=[C:16]([NH2:19])[S:17][CH:18]=1)[C:11]([NH:20][CH:21]1[C:39](=[O:40])[N:23]2[C:24]([C:36]([OH:38])=[O:37])=[C:25]([CH2:28][S:29][C:30]3[N:34]([CH3:35])[N:33]=[N:32][N:31]=3)[CH2:26][S:27][C@H:22]12)=[O:13]

参加物

8

反応物 5

HCID 10340Sodium CarbonateHCID 24819Phosphorus pentachlorideHCID 1252162-(2-Aminothiazole-4-yl)-2-methoxyiminoacetic acidHCID 516892Sodium BicarbonateHCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid

生成物 1

HCID 1317116137-[2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6344Dichloromethane溶媒

実験手順

Phosphorus pentachloride (3.3 g.) was added under ice-cooling to a suspension of 2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetic acid (syn isomer) (1.5 g.) in methylene chloride (30 ml.) and the mixture was stirred for 30 minutes at ambient temperature. Methylene chloride was distilled off under reduced pressure and acetone was added to the residue to give a suspension. On the other hand, a suspension of 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (2.2 g.) in an aqueous solution of sodium bicarbonate (0.76 g. in 50 ml. of water) was stirred for 10 minutes and acetone (50 ml.) was added thereto to give a solution. To the solution was dropwise added the above obtained suspension containing acid chloride with stirring and ice-cooling and keeping the solution at pH 7.5 to 8.5 with a 20% aqueous solution of sodium carbonate. The mixture was stirred for 1 hour at 3° to 5° C. and pH 8.0. Acetone was distilled off under reduced pressure and the residue was adjusted to pH 7.4 with a saturated aqueous solution of sodium bicarbonate and further adjusted to pH 4.5 with 10% hydrochloric acid with stirring and ice-cooling. Precipitates were filtered off and the filtrate was saturated with sodium chloride, adjusted to pH 2.5 with 10% hydrochloric acid and stirred for 1 hour. Precipitates were collected by filtration, washed with water and dried to give 7-[2-methoxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (a mixture of syn and anti isomers) (0.95 g.).

後処理

  1. distillationMethylene chloride was distilled off under reduced pressure and acetone
  2. additionwas added to the residue
  3. customto give a suspension
  4. stirringwas stirred for 10 minutes
  5. customto give a solution
  6. additionTo the solution was dropwise added the above obtained suspension
  7. stirringwith stirring
  8. temperatureice-cooling
  9. stirringThe mixture was stirred for 1 hour at 3° to 5° C.
  10. distillationAcetone was distilled off under reduced pressure
  11. stirringwith stirring
  12. temperatureice-cooling
  13. customPrecipitates
  14. filtrationwere filtered off
  15. stirringstirred for 1 hour
  16. customPrecipitates
  17. filtrationwere collected by filtration
  18. washwashed with water
  19. customdried

出典と根拠

ORDレコード
ord-c21777d647ac4d09b8f6e1b2900860cb
出典データセット
uspto-grants-1979_08
特許番号
US04166115

関連ノート

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