Hydrochloric Acid → 7-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 acid

HRID 1579217

反応式

HRID 1579217 の反応式
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[OH-].[Na+].[CH3:21][C:22]1[S:23][C:24]([SH:27])=[N:25][N:26]=1.Cl>CC(C)=O.O>[CH3:21][C:22]1[S:23][C:24]([S:27][CH2:5][C:6]2[CH2:15][S:14][CH:9]3[N:8]([C:11](=[O:12])[CH:10]3[NH2:13])[C:7]=2[C:16]([OH:18])=[O:17])=[N:25][N:26]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4413287-Aminocephalosporanic acidHCID 178434161HCID 178434161、化合物

生成物 1

HCID 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 acid

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 962Water溶媒

実験手順

A mixture of 13.6 g. (0.5 M) of 7-aminocephalosporanic acid (7-ACA) in 100 ml. of water and 50 ml. of acetone are brought to pH 8 with sodium hydroxide while stirring. 9.8 g. (0.57 M) of 2-methyl-1,3,4-thiadiazole-5-thiol are added and the mixture is heated at 80° for 4 hours. After cooling to 5°, this is acidified to pH 3.5 with dilute hydrochloric acid and stirred for 15 minutes. The precipitated solid is filtered under suction and washed with acetone. This 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]-methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is purified by dissolving in sodium bicarbonate solution and reprecipitating with 2N hydrochloric acid; yield 12.7 g., m.p. 206°.

後処理

  1. additionA mixture of 13.6 g
  2. temperaturethe mixture is heated at 80° for 4 hours
  3. temperatureAfter cooling to 5°
  4. stirringstirred for 15 minutes
  5. filtrationThe precipitated solid is filtered under suction
  6. washwashed with acetone
  7. customThis 3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]-methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid is purified
  8. dissolutionby dissolving in sodium bicarbonate solution
  9. customreprecipitating with 2N hydrochloric acid

出典と根拠

ORDレコード
ord-d755cf6ec289497a9c62f56926e36e4b
出典データセット
uspto-grants-1976_01
特許番号
US03931170

関連ノート

読み込み中…