Phosphoric Acid → HCID 178508102, compound

HRID 596765Notes

Reaction equation

HRID 596765 reaction equation
[K].[SH:2][C:3]1[NH:7][N:6]=[N:5][CH:4]=1.CC(O[CH2:12][C:13]1[CH2:22][S:21][C@@H:16]2[C@H:17]([NH2:20])[C:18](=[O:19])[N:15]2[C:14]=1[C:23]([OH:25])=[O:24])=O.C([O-])(O)=O.[Na+].P([O-])([O-])([O-])=O.OP(O)(O)=O>>[NH2:20][CH:17]1[C:18](=[O:19])[N:15]2[C:14]([C:23]([OH:25])=[O:24])=[C:13]([CH2:12][S:2][C:3]3[NH:7][N:6]=[N:5][CH:4]=3)[CH2:22][S:21][C@H:16]12

Participants

6

Reactant 5

HCID 1004Phosphoric AcidHCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178527742HCID 178527742, compound

Product 1

HCID 178508102HCID 178508102, compound

Conditions

Temperature
55 °C

Procedure

Ten grams (0.075 mole) of 5-mercapto-1,2,3-triazole potassium salt was added to a stirred slurry of 19 g. (0.07 mole) of purified 7-aminocephalosporanic acid and 5.9 g. (0.07 mole) of NaHCO3 in 350 ml. of 0.1 M phosphate buffer (pH 6.4) and the mixture heated and stirred at 55° C. for 31/2 hours under a nitrogen atmosphere. The resulting solution was cooled to 22° C. and adjusted to pH 5.5 with 40% H3PO4. The resulting precipitate was filtered off, washed with cold water (50 ml.) and air dried. The yield of 7-amino-3-(1,2,3-triazole-5-ylthiomethyl)-3-cephem-4-carboxylic acid was 8 g., dec. pt. 230° C. IR analysis showed some decomposition of the β-lactam ring but it was used "as is" for the next step.

Workup

  1. temperatureThe resulting solution was cooled to 22° C.
  2. filtrationThe resulting precipitate was filtered off
  3. washwashed with cold water (50 ml.) and air
  4. customdried

Sources & evidence

ORD record
ord-4fefe028add249a99770edf0b88f90a2
Source dataset
uspto-grants-1977_03
Patent number
US04012382

Reaction notes

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