Acetone → HCID 70604924, compound

HRID 1605269Notes

Reaction equation

HRID 1605269 reaction equation
C1(C([NH:20][CH:21]2[C:49](=[O:50])[N:23]3[CH:24]([C:29]4[N:33]([CH2:34][C:35]5[CH:40]=[CH:39][C:38]([O:41][CH2:42][C:43]6[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=6)=[CH:37][CH:36]=5)[N:32]=[N:31][N:30]=4)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.CC(C)=O>CCOCC>[NH2:20][CH:21]1[C:49](=[O:50])[N:23]2[CH:24]([C:29]3[N:33]([CH2:34][C:35]4[CH:36]=[CH:37][C:38]([O:41][CH2:42][C:43]5[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=5)=[CH:39][CH:40]=4)[N:32]=[N:31][N:30]=3)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]12

Participants

5

Reactant 3

HCID 180AcetoneHCID 521998p-Toluenesulfonic acid monohydrateHCID 70604646HCID 70604646, compound

Product 1

HCID 70604924HCID 70604924, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution consisting of 558 mg. of 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-[p-benzyloxybenzyl]tetrazol-5-yl)penam, 156 mg. of p-toluenesulfonic acid monohydrate and 1 ml. of acetone is stored at ambient temperature for 2.5 hrs. It is then added with stirring to 50 ml. of ether. After stirring for a further 10 min., the solid which precipitates is filtered. This affords 394 mg. of the p-toluenesulfonate of the product. A 304-mg. aliquot of this p-toluenesulfonate salt is dissolved in 10 ml. of methylene chloride, and to the solution is added 69.7 μl. of triethylamine. After 3 min., 5 ml. of water is added and the mixture is stirred vigorously. The organic phase is then separated off, diluted with ether, dried over anhydrous magnesium sulfate, and evaporated to dryness in vacuo. The residue is 189 mg. (69% yield) of 6-amino-2,2-dimethyl-3-(1-[p-benzyloxybenzyl]tetrazol-5-yl)penam. The NMR spectrum (in CDCl3) of the product shows absorption bands at 7.40 ppm (singlet, phenyl hydrogens), 7.15 ppm (quartet, phenylene hydrogens), 5.55 ppm (broad singlet, C-5 and benzyl hydrogens), 5.20 ppm (singlet, C-3 hydrogens), 5.10 ppm (singlet, benzyl hydrogens) 4.60 ppm (doublet, C-6 hydrogen), 1.50 ppm (singlet, C-2 methyl hydrogens) and 0.90 ppm (singlet, C-2 hydrogens).

Workup

  1. additionIt is then added
  2. stirringAfter stirring for a further 10 min.
  3. customthe solid which precipitates
  4. filtrationis filtered
  5. dissolutionaliquot of this p-toluenesulfonate salt is dissolved in 10 ml
  6. additionof methylene chloride, and to the solution is added 69.7 μl
  7. additionof water is added
  8. stirringthe mixture is stirred vigorously
  9. customThe organic phase is then separated off
  10. additiondiluted with ether
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-89731460eb204e7eb59e665ef7c13176
Source dataset
uspto-grants-1976_04
Patent number
US03950350

Reaction notes

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