Ammonia → 7-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacid

HRID 543533

Reaction equation

HRID 543533 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]([CH3:25])[N:23]=[N:22][N:21]=1.COC(C1C(Cl)=C(Cl)C(C(OC)=O)=C(Cl)C=1Cl)=O.N>C(#N)C>[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]([CH3:25])[N:23]=[N:22][N:21]=3)[CH2:15][S:14][C@H:9]12

Participants

6

Reactant 4

HCID 222AmmoniaHCID 2943DacthalHCID 4413287-Aminocephalosporanic acidHCID 178482017HCID 178482017, compound

Product 1

HCID 130208137-Amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylicacidYield 94.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A 320 ml portion of acetonitrile was added to 54.5 g of 7-ACA and 25,6 g of 5-mercapto-1-methyl-1H-tetrazole, and 296.7 g of DCPA was added to the mixture with stirring and under cooling at -20° to -10° C. After the dissolution, the reaction mixture was stirred at 15° to 17° C. for 40 minutes to allow the reaction to proceed, cooled and poured into 1.8 kg of ice-water. The mixture was allowed to stand at 5° C. overnight, cooled by adding ice under stirring and adjusted to pH 4.0 with 25% aqueous ammonia. The resulting precipitate was recovered by filtration, washed with 480 ml of cold water and 500 ml of acetone successively, and dried, thereby affording 62.2 g (94.7% of yield) of 7-amino-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid.

Workup

  1. additionwas added to the mixture
  2. temperatureunder cooling at -20° to -10° C
  3. dissolutionAfter the dissolution
  4. stirringthe reaction mixture was stirred at 15° to 17° C. for 40 minutes
  5. customthe reaction
  6. temperaturecooled
  7. temperaturecooled
  8. additionby adding ice
  9. stirringunder stirring
  10. filtrationThe resulting precipitate was recovered by filtration
  11. washwashed with 480 ml of cold water and 500 ml of acetone successively
  12. customdried

Sources & evidence

ORD record
ord-74d13e00dc9a4f928fcd1a78a53aa853
Source dataset
uspto-grants-1984_05
Patent number
US04446318

Linked notes

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