Phosphate → 7-Amino-3-[2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-one-6-ylthiomethyl]-3-cephem-4-carboxylic acid

HRID 268128Notes

Reaction equation

HRID 268128 reaction equation
CC(O[CH2:5][C:6]1[CH2:15][S:14][C@@H:9]2[C@H:10]([NH2:13])[C:11](=[O:12])[N:8]2[C:7]=1[C:16]([OH:18])=[O:17])=O.[SH:19][C:20]1[CH:21]=[CH:22][C:23]2[N:24]([C:26](=[O:29])[NH:27][N:28]=2)[N:25]=1.C(=O)(O)[O-].[Na+].P([O-])([O-])([O-])=O>>[NH2:13][CH:10]1[C:11](=[O:12])[N:8]2[C:7]([C:16]([OH:18])=[O:17])=[C:6]([CH2:5][S:19][C:20]3[CH:21]=[CH:22][C:23]4[N:24]([C:26](=[O:29])[NH:27][N:28]=4)[N:25]=3)[CH2:15][S:14][C@H:9]12

Participants

5

Reactant 4

HCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178518775HCID 178518775, compound

Product 1

HCID 1317101017-Amino-3-[2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-one-6-ylthiomethyl]-3-cephem-4-carboxylic acid

Procedure

7-ACA (1.36 g., 5 mmoles) was added at 50° C. to a solution of 6-mercapto-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-one (0.84 g., 5 mmoles) and sodium bicarbonate (0.84 g., 10 mmoles) in 20 ml. of 0.1 M phosphate buffer solution (pH 6.4) and the mixture was heated for 2 hours at 70° C. A small amount of insoluble material was removed by filtration and acidification of the filtrate to pH 5 with dil. HCl afforded the product 4e which was collected by filtration, washed with water (30 ml.) and dried in vacuo on P2O5. Yield of 7-amino-3-[2,3-dihydro-3-triazolo(4,3-b)pyridazin-3-one-6-ylthiomethyl]-3-cephem-4-carboxylic acid 1.25 g. (66%), M.p. > 300° C.

Workup

  1. customA small amount of insoluble material was removed by filtration and acidification of the filtrate to pH 5 with dil. HCl

Sources & evidence

ORD record
ord-9608bc215bb049b98e7baa16419bd1c7
Source dataset
uspto-grants-1976_03
Patent number
US03946000

Reaction notes

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