Hydrochloric Acid → HCID 131710103, compound

HRID 268130Notes

Reaction equation

HRID 268130 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[N:24]2[N:25]=[CH:26][CH:27]=[CH:28][C:23]2=[N:22][N:21]=1.C([O-])(O)=O.[Na+].P([O-])([O-])([O-])=O.Cl>>[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[N:24]4[N:25]=[CH:26][CH:27]=[CH:28][C:23]4=[N:22][N:21]=3)[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178527926HCID 178527926, compound

Product 1

HCID 131710103HCID 131710103, compound

Procedure

7-ACA (1.36 g., 5 mmole) was added portionwise to a solution of 0.68 g. (4.5 mmole) of 3-mercapto-s-triazolo[4,3-b]pyridazine and 0.84 g. (10 mmole) of NaHCO3 in 20 ml. of 0.1 M pH 7.4 phosphate buffer at 40°-50° . The mixture was heated at 80°-85° for 40 min., treated with a small amount of active carbon and acidified with dil. HCl to pH 4 to precipitate 7-amino-3-(s-triazolo[4,3-b]pyridazin-3-ylthiomethyl)-3-cephem-4-carboxylic acid which was collected, washed with 20 ml. of water and dried in vacuo on P2O5 to yield 0.81 g. (49%), M.p. > 300°.

Workup

  1. customat 40°-50°
  2. temperatureThe mixture was heated at 80°-85° for 40 min.
  3. additiontreated with a small amount of active carbon
  4. customto precipitate 7-amino-3-(s-triazolo[4,3-b]pyridazin-3-ylthiomethyl)-3-cephem-4-carboxylic acid which
  5. customwas collected
  6. washwashed with 20 ml
  7. dry with materialof water and dried in vacuo on P2O5
  8. customto yield 0.81 g

Sources & evidence

ORD record
ord-536150a5cd1b4e738298c7809e09a0b1
Source dataset
uspto-grants-1976_03
Patent number
US03946000

Reaction notes

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