Phosphoric Acid → HCID 88841051, compound

HRID 1287813Notes

Reaction equation

HRID 1287813 reaction equation
[S:1]1[CH:5]=[C:4]([C:6](=[S:8])[O-:7])[N:3]=[CH:2]1.[K+].P([O-])([O-])([O-])=O.CC(O[CH2:19][C:20]1[CH2:29][S:28][C@@H:23]2[C@H:24]([NH2:27])[C:25](=[O:26])[N:22]2[C:21]=1[C:30]([OH:32])=[O:31])=O.C([O-])(O)=O.[Na+].OP(O)(O)=O>>[NH2:27][CH:24]1[C:25](=[O:26])[N:22]2[C:21]([C:30]([OH:32])=[O:31])=[C:20]([CH2:19][S:8][C:6]([C:4]3[N:3]=[CH:2][S:1][CH:5]=3)=[O:7])[CH2:29][S:28][C@H:23]12

Participants

6

Reactant 5

HCID 1004Phosphoric AcidHCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 23711268HCID 23711268, compound

Product 1

HCID 88841051HCID 88841051, compound

Procedure

A solution of 68% potassium thiazole-4-thiocarboxylate (5.4 g., 0.02 mole) in 100 ml. water was washed with 100 ml. of ether and then 200 ml. of pH 6.4 phosphate buffer and 7-aminocephalosporanic acid (5.5 g., 0.02 mole) was added. The mixture was heated at 48° for 4 hours as the pH was kept at 6.4 with NaHCO3 solution. The solution was then cooled and acidified with 40% H3PO4 to pH 5.2. The product was collected by filtration, washed with water and acetone, and air dried overnight to yield 3.0 g. The material was not further purified and IR and NMR spectra were consistent with required structure.

Workup

  1. washwater was washed with 100 ml
  2. temperatureThe mixture was heated at 48° for 4 hours as the pH
  3. temperatureThe solution was then cooled
  4. filtrationThe product was collected by filtration
  5. washwashed with water and acetone, and air
  6. customdried overnight
  7. customto yield 3.0 g
  8. customThe material was not further purified

Sources & evidence

ORD record
ord-7e84bd4a7c934b2b9ee9d8defd728853
Source dataset
uspto-grants-1976_10
Patent number
US03985740

Reaction notes

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