Ammonia → 7-Amino-3-(4,6-diamino-1-ethylpyrimidinium-2-yl)thiomethyl-3-cephem-4-carboxylate

HRID 847424노트

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HRID 847424 반응식
C(O[CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH2:17])[C:15](=[O:18])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=O)C.[NH2:19][C:20]1[CH:25]=[C:24]([NH2:26])[N:23]([CH2:27][CH3:28])[C:22](=[S:29])[N:21]=1.CO.N>O1CCOCC1>[NH2:17][CH:16]1[C:15](=[O:18])[N:10]2[C:11]([C:12]([O-:14])=[O:13])=[C:6]([CH2:5][S:29][C:22]3[N:21]=[C:20]([NH2:19])[CH:25]=[C:24]([NH2:26])[N+:23]=3[CH2:27][CH3:28])[CH2:7][S:8][C@H:9]12

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 887MethanolHCID 113463103-Acetoxymethyl-7-amino-3cephem-4-carboxylic acidHCID 152003604,6-diamino-1-ethyl-2-(1H)-pyrimidinethione

생성물 1

HCID 677876667-Amino-3-(4,6-diamino-1-ethylpyrimidinium-2-yl)thiomethyl-3-cephem-4-carboxylate수율 75.1%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
0 °C

실험 절차

Under an anhydrous condition, a solution containing 2.72 g of 3-acetoxymethyl-7-amino-3cephem-4-carboxylic acid and 1.8 g of 4,6-diamino-1-ethyl-2-(1H)-pyrimidinethione suspended in 20 ml of dry dioxane was cooled to 0° C.; and 3 ml of boron trifluoride diethylether was added. The temperature of the reaction solution was increased to 40° C.; the solution was stirred for one hour; and then 10 ml of methyl alcohol was added. The resultant solution was stirred for 10 minutes and was added with 30 ml of ice water. The pH of the solution was adjusted to 7.1 by adding aqueous ammonia solution After concentration under a reduced pressure, e.g., about 20 mmHg, the solution was adjusted to pH 3.6 with 2N-aqueous hydrochloric acid; and allowed to stand at a room temperature for 24 hrs. The precipitates resulted from the reaction solution were filtered, washed with 10 ml of distilled water and with 10 ml of methyl alcohol, and dried to give 2.87 g of the title compound as a solid.

후처리

  1. temperatureThe temperature of the reaction solution was increased to 40° C.
  2. concentrationAfter concentration under a reduced pressure, e.g., about 20 mmHg
  3. waitto stand at a room temperature for 24 hrs
  4. customThe precipitates resulted from the reaction solution
  5. filtrationwere filtered
  6. washwashed with 10 ml of distilled water and with 10 ml of methyl alcohol
  7. customdried

출처 및 근거

ORD 기록
ord-54616e75376649cfa9f41b4409ef01f3
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05142041

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