Perchloric Acid → HCID 131710504, compound

HRID 1287998Notes

Reaction equation

HRID 1287998 reaction equation
C(O[CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:28])[C:16]([O:26][CH3:27])([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C@H:9]2[S:8][CH:7]=1)(=O)N.Cl(O)(=O)(=O)=O.[NH:34]=[N+:35]=[N-:36]>O1CCCC1.C(Cl)Cl>[N:34]([CH2:5][C:6]1[CH:11]([C:12]([OH:14])=[O:13])[N:10]2[C:15](=[O:28])[C:16]([O:26][CH3:27])([NH:17][C:18](=[O:25])[CH2:19][C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)[C@H:9]2[S:8][CH:7]=1)=[N+:35]=[N-:36]

Participants

6

Reactant 3

HCID 24247Perchloric AcidHCID 24530Hydrazoic acidHCID 68131458HCID 68131458, compound

Product 1

HCID 131710504HCID 131710504, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the benzhydryl ester of 3-carbamoyloxymethyl-7-methoxy-7-(2-thienylacetamido)-2-cephem-4-carboxylic acid (0.212 g.), perchloric acid (0.36 g.) in tetrahydrofuran (6.0 ml.) and hydrazoic acid (28.0 ml., 0.18 N) in methylene chloride is stirred under a nitrogen atmosphere for nine hours. The reaction mixture is washed with a 5% aqueous sodium bicarbonate solution and then with a saturated sodium chloride solution. The methylene chloride solution is dried over anhydrous sodium sulfate, filtered and the solvent removed by evaporation. The crude product is purified by chromatographing through a column of silica gel G to yield the substantially pure benzhydryl ester of 3-azidomethyl-7-methoxy-7-(2-thienylacetamido)-2-cephem-4-carboxylic acid.

Workup

  1. washThe reaction mixture is washed with a 5% aqueous sodium bicarbonate solution
  2. dry with materialThe methylene chloride solution is dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customthe solvent removed by evaporation
  5. customThe crude product is purified by chromatographing through a column of silica gel G

Sources & evidence

ORD record
ord-b3bbb0174336419399524292d8b3d789
Source dataset
uspto-grants-1976_10
Patent number
US03987040

Reaction notes

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