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

HRID 1731225Notes

Reaction equation

HRID 1731225 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-16098dfe3c3e4f3da253a2d78e1e663f
Source dataset
uspto-grants-1976_11
Patent number
US03994939

Reaction notes

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