Perchloric Acid → HCID 15593985, compound

HRID 1415118Notes

Reaction equation

HRID 1415118 reaction equation
[NH2:1][CH:2]1[C:9](=[O:10])[N:8]2[CH:3]1[S:4][CH2:5][C:6]([CH2:14][S:15][C:16]1(C)[S:20]CN=[N:17]1)=[C:7]2[C:11]([OH:13])=[O:12].Cl(O)(=O)(=O)=O.C(=O)(O)[O-].[K+].[NH2:32][CH:33]1C(=O)N2[CH:34]1SCC(CSC1SC(C)=NN=1)=C2C(OC(C1C=CC=CC=1)C1C=CC=CC=1)=O>O.O1CCCC1>[CH3:34][C:33]1[N:17]=[C:16]([S:15][CH2:14][C:6]2[CH2:5][S:4][CH:3]3[N:8]([C:9](=[O:10])[CH:2]3[NH2:1])[C:7]=2[C:11]([OH:13])=[O:12])[S:20][N:32]=1

Participants

7

Reactant 4

HCID 24247Perchloric Acid2×HCID 516893Potassium BicarbonateHCID 12796637HCID 12796637, compoundHCID 86734402HCID 86734402, compound

Product 1

HCID 15593985HCID 15593985, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

18 g. of 7-amino-3-[[(5-methyl-1,3,4-thiadiazol-5-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid are suspended in 350 ml. of tetrahydrofuran. 4.1 ml. of 70% perchloric acid are added dropwise. After 30 minutes, a slightly turbid solution forms. This solution is filtered and to the filtrate is added dropwise with stirring 12 g. of diphenyldiazomethane and 20 ml. of tetrahydrofuran. After three hours, the reaction mixture is poured into 2 liters of absolute ether. The solid, light brown precipitate, which is the perchloric acid salt of the desired product, is dried over Kieselgel in a desiccator. To obtain the base, the perchloric acid salt is dissolved in water and treated with the calculated equivalent of potassium bicarbonate. The aqueous solution obtained is extracted with chloroform. The chloroform phase is treated with activated carbon and sodium sulfate to obtain the 10 g. of the product, 7-amino-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2 -ene-2-carboxylic acid, diphenylmethyl ester, as a light brown powder, m.p. 157°-159°. The product is recrystallized from tetrahydrofuran/petroleum ether. The isomeric thiadiazolyl derivative is similarly obtained from the product of Example 20.

Workup

  1. filtrationThis solution is filtered and to the filtrate
  2. additionis added dropwise
  3. waitAfter three hours
  4. additionthe reaction mixture is poured into 2 liters of absolute ether
  5. customis dried over Kieselgel in a desiccator
  6. customTo obtain the base
  7. customThe aqueous solution obtained
  8. extractionis extracted with chloroform
  9. additionThe chloroform phase is treated with activated carbon and sodium sulfate
  10. customto obtain the 10 g
  11. customThe product is recrystallized from tetrahydrofuran/petroleum ether

Sources & evidence

ORD record
ord-c46183835f634c719a8b6397e665bc14
Source dataset
uspto-grants-1977_01
Patent number
US04003893

Reaction notes

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