Acetic Acid → 2-Methyl-7-[2-(1,3,4-thiadiazol-2-ylthio)-acetamido]-3-cephem-4-carboxylic acid

HRID 1764029ノート

反応式

HRID 1764029 の反応式
C(O)(=O)C.[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([O:14]CC(Cl)(Cl)Cl)=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][S:25][C:26]3[S:27][CH:28]=[N:29][N:30]=3)[C@H:8]2[S:7]1.C(OCC)(=O)C>CN(C)C=O.[Zn]>[CH3:5][CH:6]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[N:9]2[C:20](=[O:32])[CH:21]([NH:22][C:23](=[O:31])[CH2:24][S:25][C:26]3[S:27][CH:28]=[N:29][N:30]=3)[C@H:8]2[S:7]1

参加物

6

反応物 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 128340152,2,2-Trichloroethyl 2-methyl-7-[2-(1,3,4-thiadiazol-2-yithio)acetamido]-3-cephem-4-carboxylate

生成物 1

HCID 128340182-Methyl-7-[2-(1,3,4-thiadiazol-2-ylthio)-acetamido]-3-cephem-4-carboxylic acid収率 43.6%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 6228Dimethylformamide溶媒

実験手順

Acetic acid (8 ml) and zinc powder (6 g) were added under stirring and ice-cooling to a solution of 2,2,2-trichloroethyl 2-methyl-7-[2-(1,3,4-thiadiazol-2-ylthio)acetamido]-3-cephem-4-carboxylate (4.65 g) in anhydrous dimethylformamide (30 ml), and the mixture was stirred for 1 hour at the same temperature. After the reaction, ethyl acetate (150 ml) was added to the reaction mixture. The insoluble material was filtered off, and the filtrate was washed with 5% hydrochloric acid saturated with sodium chloride, and then extracted with a sodium bicarbonate aqueous solution. The extract was acidified with 10% hydrochloric acid and extracted with ethyl acetate, after which the ethyl acetate layer was washed with a saturated sodium chloride aqueous solution and dried over magnesium sulfate. After the solvent was distilled off, the residue was recrystallized from a mixture of ethyl acetate and benzene to give 2-methyl-7-[2-(1,3,4-thiadiazol-2-ylthio)acetamido]-3-cephem-4-carboxylic acid (1.5 g), mp 197° to 199° C.

後処理

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. additionwas added to the reaction mixture
  3. filtrationThe insoluble material was filtered off
  4. washthe filtrate was washed with 5% hydrochloric acid saturated with sodium chloride
  5. extractionextracted with a sodium bicarbonate aqueous solution
  6. extractionextracted with ethyl acetate
  7. washafter which the ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over magnesium sulfate
  9. distillationAfter the solvent was distilled off
  10. customthe residue was recrystallized from a mixture of ethyl acetate and benzene

出典と根拠

ORDレコード
ord-bef851bc04ae4b0dbad0ad2689fd23be
出典データセット
uspto-grants-1978_09
特許番号
US04113940

反応ノート

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