Pyridine → HCID 70605068, compound

HRID 614132Notes

Reaction equation

HRID 614132 reaction equation
[C:1]1([C:7]([NH:20][CH:21]2[C:38](=[O:39])[N:23]3[CH:24]([C:29](=O)[NH:30][CH2:31][C:32]4[O:36][CH:35]=[CH:34][CH:33]=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.N1C=CC=CC=1.C(Cl)(Cl)=O.[N-:50]=[N+:51]=[N-:52].CN(C)C(=[NH2+])N(C)C>C(Cl)(Cl)Cl.O>[C:1]1([C:7]([NH:20][CH:21]2[C:38](=[O:39])[N:23]3[CH:24]([C:29]4[N:30]([CH2:31][C:32]5[O:36][CH:35]=[CH:34][CH:33]=5)[N:52]=[N:51][N:50]=4)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=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

Participants

7

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 70604744HCID 70604744, compoundHCID 178484365HCID 178484365, compound

Product 1

HCID 70605068HCID 70605068, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent4×

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 3.05 g. (5.7 mmole) of 6-(triphenylmethylamino)-2,2-dimethyl-3-(N-furfurylcarbamoyl)penam, in 8 ml. of chloroform, at 0° C., is added 1.35 ml. (17 mmole) of pyridine, followed by 2.64 ml. of a 4.33 M solution of phosgene in chloroform. Stirring is then continued for 1 hour at 25° C. The chloroform, and excess phosgene and pyridine, are then removed by evaporation in vacuo, and the residue is redissolved in 5 ml. of chloroform. The solution is cooled to 0° C., and then 2.25 g. (14.4 mmole) of tetramethylguanidinium azide is added in several small portions. Stirring is continued for 15 minutes at ambient temperature, and then 20 ml. of chloroform, followed by 30 ml. of water, are added and the pH is adjusted to 6.5. The chloroform layer is separated off, washed with water, followed by brine, and then dried (MgSO4). Removal of the solvent by evaporation in vacuo leaves 3.37 g. of a dark-red foam. The foam is re-dissolved in a small volume of chloroform and absorbed onto a column of chromatographic silica gel. Elution of the column with chloroform, followed by evaporation of the appropriate fractions in vacuo, affords 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-furfuryltetrazol-5-yl)penam. The NMR spectrum of the product (CDCl3) shows absorptions at 7.40 ppm (m, 16H), 6.40 ppm (m, 2H), 5.50 ppm (s, 2H), 5.20 ppm (s, 1H), 4.90 ppm (m, 2H), 1.60 ppm (s, 3H), and 0.80 ppm (s, 3H).

Workup

  1. customThe chloroform, and excess phosgene and pyridine, are then removed by evaporation in vacuo
  2. dissolutionthe residue is redissolved in 5 ml
  3. stirringStirring
  4. waitis continued for 15 minutes at ambient temperature
  5. customThe chloroform layer is separated off
  6. washwashed with water
  7. dry with materialdried (MgSO4)
  8. customRemoval of the solvent
  9. customby evaporation in vacuo
  10. customleaves 3.37 g
  11. customabsorbed onto a column of chromatographic silica gel
  12. washElution of the column with chloroform
  13. customfollowed by evaporation of the appropriate fractions in vacuo

Sources & evidence

ORD record
ord-76563ddbfac347beb89945c08c65b2c5
Source dataset
uspto-grants-1979_03
Patent number
US04143039

Reaction notes

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