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

HRID 847423노트

반응식

HRID 847423 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]([CH3:27])[C:22](=[S:28])[N:21]=1.CO.N>C(#N)C>[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:28][C:22]3[N:21]=[C:20]([NH2:19])[CH:25]=[C:24]([NH2:26])[N+:23]=3[CH3:27])[CH2:7][S:8][C@H:9]12

참가 물질

6

반응물 4

HCID 222AmmoniaHCID 887MethanolHCID 110081672(1H)-Pyrimidinethione, 4,6-diamino-1-methyl-HCID 113463103-Acetoxymethyl-7-amino-3cephem-4-carboxylic acid

생성물 1

HCID 677883687-Amino-3-(4,6-diamino-1-methyl-pyrimidinium-2-yl)thiomethyl-3-cephem-4-carboxylate수율 73.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
0 °C

실험 절차

Under an anhydrous condition, a solution containing 2.72 g of 3-acetoxymethyl-7-amino-3-cephem-4-carboxylic acid and 1.56 g of 4,6-diamino-1-methyl-2-(1H)pyrimidinethione suspended in 20 ml of dry acetonitrile was cooled to 0° C.; and 3.6 ml of boron trifluoride diethylether was added. The temperature of the reaction solution was increased to a room temperature, e.g., 18°-20° C.; the solution was stirred for three hours; 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 3.7 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 2.69 g of the title compound as a solid.

후처리

  1. temperatureThe temperature of the reaction solution was increased to a room temperature
  2. custome.g., 18°-20° C.
  3. concentrationAfter concentration under a reduced pressure, e.g., about 20 mmHg
  4. waitto stand at a room temperature for 24 hrs
  5. customThe precipitates resulted from the reaction solution
  6. filtrationwere filtered
  7. washwashed with 10 ml of distilled water and with 10 ml of methyl alcohol
  8. customdried

출처 및 근거

ORD 기록
ord-f878150a6292476c825b248e06fba628
출처 데이터셋
uspto-grants-1992_08
특허 번호
US05142041

반응 노트

불러오는 중…