Diazabicyclo[4.3.0]non-5-ene → 6(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam

HRID 614140노트

반응식

HRID 614140 반응식
[C:1]1([C:7]([NH:20][CH:21]2[C:40](=[O:41])[N:23]3[CH:24]([C:29]4[N:33](CCC(OC)=O)[N:32]=[N:31][N:30]=4)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N12CCCC1=CCCN2>C(Cl)(Cl)Cl>[C:1]1([C:7]([NH:20][CH:21]2[C:40](=[O:41])[N:23]3[CH:24]([C:29]4[NH:30][N:31]=[N:32][N:33]=4)[C:25]([CH3:27])([CH3:28])[S:26][C@H:22]23)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 21585024Diazabicyclo[4.3.0]non-5-eneHCID 706051756-(Triphenylmethylamino)-2,2-dimethyl-3-(1-[2-methoxycarbonylethyl]tetrazol-5-yl)penam

생성물 1

HCID 1784319216(Triphenylmethylamino)-2,2-dimethyl-3-(5-tetrazolyl)penam수율 71%

시약·촉매·용매 1

HCID 6212Chloroform용매3회

실험 절차

To a stirred solution of 600 mg. of 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-[2-methoxycarbonylethyl]tetrazol-5-yl)penam (containing ca 4.5% of methanol) in 1 ml. of chloroform, is added a solution of 375.2 mg. of diazabicyclo[4.3.0]non-5-ene in 0.5 ml. of chloroform. Stirring is continued for a further 3 hours, and then the solution is diluted with a further 2 ml. of chloroform. The latter solution is washed quickly with 5 ml. of 2N hydrochloric acid, and then a further 5 ml. of 2N hydrochloric are added. The resulting mixture is cooled to ca 0° C., and the solid which precipitates is filtered off, giving 323 mg. (71% yield) of the title compound. The NMR spectrum (DMSO-d6) of the product shows absorptions at 7.40 ppm(m, 15H), 5.30 ppm (s, 1H), 4.60 ppm (m, 2H), 1.58 ppm (s, 3H) and 0.78 ppm (s, 3H).

후처리

  1. additionthe solution is diluted with a further 2 ml
  2. washThe latter solution is washed quickly with 5 ml
  3. additionof 2N hydrochloric are added
  4. temperatureThe resulting mixture is cooled to ca 0° C.
  5. customthe solid which precipitates
  6. filtrationis filtered off
  7. customgiving 323 mg

출처 및 근거

ORD 기록
ord-fe88065635ad4164b5723fef93e90eb2
출처 데이터셋
uspto-grants-1979_03
특허 번호
US04143039

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