Hydrochloric Acid → 7-Amino-3-(pyrido[2,1-c]-s-triazol-3-ylthiomethyl)-3-cephem-4-carboxylic Acid

HRID 1155509Notes

Reaction equation

HRID 1155509 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.C(=O)(O)[O-].[Na+].[SH:24][C:25]1[N:26]2[CH:33]=[CH:32][CH:31]=[CH:30][C:27]2=[N:28][N:29]=1.Cl>O.CC(C)=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:24][C:25]3[N:26]4[CH:33]=[CH:32][CH:31]=[CH:30][C:27]4=[N:28][N:29]=3)[CH2:15][S:14][C@H:9]12

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178527925HCID 178527925, compound

Product 1

HCID 1317101027-Amino-3-(pyrido[2,1-c]-s-triazol-3-ylthiomethyl)-3-cephem-4-carboxylic AcidYield 63.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

2.72 g (0.01 mol) of 7-aminocephalosporanic acid was suspended in 18 ml of water, and a suspension of 2.1 g (0.025 mol) of sodium bicarbonate in 20 ml of water was added dropwise thereto over a period of time of 10 minutes. The inside temperature of the reactor was then increased to 50° C., and a suspension of 1.81 g (0.0125 mol) of 3-mercaptopyrido[2,1-c]-s-triazole in 35 ml of acetone was added dropwise thereto over a period of time of 10 minutes. The resulting mixture was refluxed for 4 hours at a stable inside temperature of the reactor of 63° C. followed by ice cooling the mixture. After the inside temperature of the reactor reached 4° C., the mixture was adjusted to a pH of 3.6 with 6 N hydrochloric acid. One hour after the stirring, the precipitated crystals were filtered and dried over phosphorus pentoxide under reduced pressure to obtain 2.31 g (yield: 61%) of the titled compound having a melting point (decomposition) of 173° to 175° C.

Workup

  1. additionwas added dropwise
  2. additionwas added dropwise
  3. waitover a period of time of 10 minutes
  4. temperatureThe resulting mixture was refluxed for 4 hours at a stable inside temperature of the reactor of 63° C.
  5. customreached 4° C.
  6. filtrationOne hour after the stirring, the precipitated crystals were filtered
  7. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-c2fcca23557e4b8cb091bd3a6cdf956e
Source dataset
uspto-grants-1981_11
Patent number
US04302454

Reaction notes

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