Hydrochloric Acid → HCID 21426449、化合物

HRID 258705ノート

反応式

HRID 258705 の反応式
C(O[CH2:5][C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:26])[CH:10]2[NH:14][C:15](=[O:25])[CH2:16][N:17]2[CH:21]=[CH:20][N:19]=[C:18]2[S:22]([CH3:24])=[O:23])[C:7]=1[C:27]([OH:29])=[O:28])(=O)C.C(=O)(O)[O-].[Na+].[CH3:35][C:36]1[S:37][C:38](=[S:41])[NH:39][N:40]=1.Cl>O>[C:27]([C:7]1[N:8]2[CH:11]([S:12][CH2:13][C:6]=1[CH2:5][S:41][C:38]1[S:37][C:36]([CH3:35])=[N:40][N:39]=1)[CH:10]([NH:14][C:15](=[O:25])[CH2:16][N:17]1[CH:21]=[CH:20][N:19]=[C:18]1[S:22]([CH3:24])=[O:23])[C:9]2=[O:26])([OH:29])=[O:28]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2 回HCID 18102035-Methyl-1,3,4-thiadiazole-2(3H)-thioneHCID 21426442HCID 21426442、化合物

生成物 1

HCID 21426449HCID 21426449、化合物収率 27.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
60 °C

実験手順

3-Acetoxymethyl-2-carboxy-7-[(2-methylsulphinylimidazol-1-yl)-acetamido]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]-oct-2-ene (8.5 g.) and sodium bicarbonate (1.62 g.) are dissolved in water (75 cc.). A solution of 2-methyl-5-thioxo-1,3,4-thiadiazoline (2.54 g.) and sodium bicarbonate (1.62 g.) in water (75 cc.) is added and the mixture is heated at 60° C. for 6 hours. After cooling, the pH is adjusted to 6 by adding hydrochloric acid (4 N) and the mixture is washed twice with ethyl acetate (a total of 200 cc.). The mixture is acidified to pH 2 by adding hydrochloric acid (4 N); a product precipitates and is filtered off and dried under reduced pressure (1 mm.Hg) to give 7.9 g. of product. Recrystallisation from methanol (25 cc.), filtration and drying under reduced pressure (0.1 mm.Hg) gives 2-carboxy-3-[(5-methyl-1,3,4-thiadiazol-2-yl)-thiomethyl]-7-[(2-methylsulphinyl-imidazol-1-yl)-acetamido]-8-oxo-5-thia-1-aza-bicyclo[4,2,0]oct-2-ene (2.7 g.), m.p. 227° C. (with decomposition), [α]D20 = -35° ± 1° (c= 1, dimethylformamide).

後処理

  1. temperatureAfter cooling
  2. washthe mixture is washed twice with ethyl acetate (a total of 200 cc
  3. additionby adding hydrochloric acid (4 N)
  4. customa product precipitates
  5. filtrationis filtered off
  6. customdried under reduced pressure (1 mm.Hg)
  7. customto give 7.9 g
  8. customRecrystallisation
  9. filtrationfrom methanol (25 cc.), filtration
  10. customdrying under reduced pressure (0.1 mm.Hg)

出典と根拠

ORDレコード
ord-a4e1b44022af4feaa72a302e5bdb4dc0
出典データセット
uspto-grants-1977_07
特許番号
US04034088

反応ノート

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