Methane → HCID 178434147, compound

HRID 1730866Notes

Reaction equation

HRID 1730866 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[NH:24][C:23]([CH3:25])=[N:22][N:21]=1.P([O-])([O-])([O-])=O.C([O-])(O)=O.[Na+].C.Cl>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:19][C:20]3[NH:24][C:23]([CH3:25])=[N:22][N:21]=3)[CH2:15][S:14][C@H:9]12

Participants

8

Reactant 6

HCID 297MethaneHCID 313Hydrochloric AcidHCID 1061PhosphateHCID 4413287-Aminocephalosporanic acidHCID 516892Sodium BicarbonateHCID 178434157HCID 178434157, compound

Product 1

HCID 178434147HCID 178434147, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

7-ACA (13.65 g) and 5-mercapto-2-methyl-1,3,4-triazole (8.15 g) are suspended in 500 ml. of phosphate buffer 0.2 M (Na2HPO4 /NaH2PO4) pH 6.5. To the suspension are added with stirring 10.93 g. of NaHCO3. The reaction medium is heated for 80 minutes with stirring on a 80° C water bath. The solution is then treated with charcoal, cooled (5°-10° C) and acidified to pH 4 with 2 N hydrochloric acid. The obtained suspension is diluted with 150 ml. of acetone and stirred for 30 minutes. The precipitate is filtered, washed with water, acetone and ethyl ether and dried under reduced pressure to yield 7-amino-3-(2-methyl-1,3,4-triazol-5-ylthiomethyl)-3-cephem-4 -carboxylic acid.

Workup

  1. additionTo the suspension are added
  2. temperatureThe reaction medium is heated for 80 minutes
  3. stirringwith stirring on a 80° C water bath
  4. temperaturecooled (5°-10° C)
  5. additionThe obtained suspension is diluted with 150 ml
  6. filtrationThe precipitate is filtered
  7. washwashed with water, acetone and ethyl ether
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-282aab1c1ba7461ebf1207028b6d7b96
Source dataset
uspto-grants-1976_11
Patent number
US03994886

Reaction notes

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