Phosphoric Acid → 7beta-(Thienylacetamido)-3-azidomethyl-3-cephem-4-carboxylic acid

HRID 28020Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:39](=[O:40])[N:12]2[C:13]([C:36]([OH:38])=[O:37])=[C:14]([CH2:17]OC(=O)C3C=CC=CC=3S(=O)(=O)NC(OCC)=O)[CH2:15][S:16][C@H:11]12)=[O:8].[N-:41]=[N+:42]=[N-:43].[Na+].C(=O)(O)[O-].[Na+].P(=O)(O)(O)O>P([O-])([O-])([O-])=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C@@H:10]1[C:39](=[O:40])[N:12]2[C:13]([C:36]([OH:38])=[O:37])=[C:14]([CH2:17][N:41]=[N+:42]=[N-:43])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

7β-(Thienylacetamido)-3-[2-(N-carboethoxysulfamoyl)-benzoyloxy]methyl-3-cephem-4-carboxylic acid-etherate (619 mg), sodium azide (100 mg) and sodium bicarbonate (84 mg) are dissolved in phosphate buffer solution (pH 6.4) (10 ml) and the mixture is stirred at 60° C. for one hour. After cooling, the reaction mixture is acidified by phosphoric acid and extracted with ethyl acetate. The ethyl acetate layer is dried and concentrated under reduced pressure. The residue is triturated with ether. The procedure provides 7β-(thienylacetamido)-3-azidomethyl-3-cephem-4-carboxylic acid.

Workup

temperatureAfter cooling
extractionextracted with ethyl acetate
dry with materialThe ethyl acetate layer is dried
concentrationconcentrated under reduced pressure
customThe residue is triturated with ether

Sources & evidence

ORD record: ord-5bcec5459bea4f9280758bd1ed364f42
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04224441

Reaction notes

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