Hydrochloric Acid → HCID 21426449, 화합물

HRID 258705노트

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HRID 258705 반응식
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]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 516892Sodium Bicarbonate2회HCID 18102035-Methyl-1,3,4-thiadiazole-2(3H)-thioneHCID 21426442HCID 21426442, 화합물

생성물 1

HCID 21426449HCID 21426449, 화합물수율 27.3%

시약·촉매·용매 1

HCID 962Water용매2회

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온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a4e1b44022af4feaa72a302e5bdb4dc0
출처 데이터셋
uspto-grants-1977_07
특허 번호
US04034088

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