Phosphate → HCID 178508100, compound

HRID 268125Notes

Reaction equation

HRID 268125 reaction equation
[OH:1][C:2]1[N:3]=[N:4][C:5]([SH:8])=[CH:6][CH:7]=1.CC(O[CH2:13][C:14]1[CH2:23][S:22][C@@H:17]2[C@H:18]([NH2:21])[C:19](=[O:20])[N:16]2[C:15]=1[C:24]([OH:26])=[O:25])=O.C(=O)(O)[O-].[Na+].P([O-])([O-])([O-])=O>>[NH2:21][CH:18]1[C:19](=[O:20])[N:16]2[C:15]([C:24]([OH:26])=[O:25])=[C:14]([CH2:13][S:8][C:5]3[N:4]=[N:3][C:2]([OH:1])=[CH:7][CH:6]=3)[CH2:23][S:22][C@H:17]12

Participants

5

Reactant 4

HCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178516308HCID 178516308, compound

Product 1

HCID 178508100HCID 178508100, compound

Procedure

A mixture of 0.60 g. (0.0047 mole) of 3-hydroxy-6-mercaptopyridazine, 1.27 g. (0.0047 mole) of 7-aminocephalosporanic acid, 0.78 g. (0.0094 mole) of sodium bicarbonate in 25 ml. of 0.1 M phosphate buffer (pH 6.4) was heated at 60° C. for 5 hours. The reaction mixture was filtered to remove a trace of insoluble material and the filtrate was adjusted to pH 5 with acetic acid to give brown precipitates, which were collected by filtration, washed with water and acetone successively and dried in vacuo to give 7-amino-3-(6-hydroxypyridazin-3-ylthiomethyl)-3-cephem-4-carboxylic acid; 1.03 g. (71%). M.p. 290°-300° C. (decomp.).

Workup

  1. additionA mixture of 0.60 g
  2. filtrationThe reaction mixture was filtered
  3. customto remove a trace of insoluble material
  4. customto give brown precipitates, which
  5. filtrationwere collected by filtration
  6. washwashed with water and acetone successively
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7a7c107c33b04e07ad469af697dec261
Source dataset
uspto-grants-1976_03
Patent number
US03946000

Reaction notes

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