Pyridine → 6-(Triphenylmethylamino)-2,2-dimethyl-3-(1-[4-acetoxybenzyl]tetrazol-5-yl)penam

HRID 1731220Notes

Reaction equation

HRID 1731220 reaction equation
[C:1]1([C:7]([NH:20][CH:21]2[C:40](=[O:41])[N:23]3[CH:24]([C:29](=O)[NH:30][CH2:31][C:32]4[CH:37]=[CH:36][C:35]([OH:38])=[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:48](Cl)(=[O:50])[CH3:49].C(Cl)(Cl)=O.[N-:56]=[N+:57]=[N-:58].CN(C)C(=[NH2+])N(C)C.[OH-].[Na+]>O.C(Cl)(Cl)Cl>[C:14]1([C:7]([NH:20][CH:21]2[C:40](=[O:41])[N:23]3[CH:24]([C:29]4[N:30]([CH2:31][C:32]5[CH:37]=[CH:36][C:35]([O:38][C:48](=[O:50])[CH3:49])=[CH:34][CH:33]=5)[N:58]=[N:57][N:56]=4)[C:25]([CH3:28])([CH3:27])[S:26][C@H:22]23)([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

9

Reactant 6

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 6371PhosgeneHCID 14798Sodium HydroxideHCID 706048796-(triphenylmethylamino)-2,2-dimethyl-3-(N-[4-hydroxybenzyl]carbamoyl)penamHCID 178484365HCID 178484365, compound

Product 1

HCID 681375066-(Triphenylmethylamino)-2,2-dimethyl-3-(1-[4-acetoxybenzyl]tetrazol-5-yl)penam

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Conditions

Temperature
4 °C

Procedure

To a stirred solution of 1.69 g. (3 mmole) of 6-(triphenylmethylamino)-2,2-dimethyl-3-(N-[4-hydroxybenzyl]carbamoyl)penam in 9 ml. of chloroform is added 1 ml. (12 mmole) of pyridine. The solution is cooled to ca. 4° C. in an ice-bath and 235 mg. of acetyl chloride is added slowly. The solution is stirred for 2 hours at ambient temperature, and then it is again cooled to ca. 4° C. Phosgene (1.5 ml. of a 4.3 M solution in chloroform [6.45 mmole]) is added and the cooling bath is removed. Stirring is continued for a further 1.5 hours, and then all the volatile components are removed by evaporation in vacuo. The residue is redissolved in 6 ml. of chloroform and the solution is cooled to ca. 4° C. in an ice-bath. To the stirred solution is added 0.95 g. (6 mmole) of tetramethylguanidinium azide, and then stirring is continued for a further 1 hour at ambient temperature. At this point, 25 ml. of water is added, followed by sufficient 1N sodium hydroxide to bring the pH of the aqueous phase to 10. The chloroform layer is separated off, washed with water, dried using sodium sulfate, and evaporated to dryness in vacuo. This affords crude 6-(triphenylmethylamino)-2,2-dimethyl-3-(1-[4-acetoxybenzyl]tetrazol-5-yl)penam, which is purified further by chromatography.

Workup

  1. temperatureit is again cooled to ca. 4° C
  2. customthe cooling bath is removed
  3. stirringStirring
  4. waitis continued for a further 1.5 hours
  5. customall the volatile components are removed by evaporation in vacuo
  6. dissolutionThe residue is redissolved in 6 ml
  7. temperatureof chloroform and the solution is cooled to ca. 4° C. in an ice-bath
  8. additionTo the stirred solution is added 0.95 g
  9. waitis continued for a further 1 hour at ambient temperature
  10. customThe chloroform layer is separated off
  11. washwashed with water
  12. customdried
  13. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-903058b1b9ee4be2b208acae48948574
Source dataset
uspto-grants-1976_11
Patent number
US03994939

Reaction notes

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