Ammonia → 7-Amino-3-(1,4,6-triaminopyrimidinium-2-yl)thiomethyl-3-cephem-4-carboxylate

HRID 847425Notes

Reaction equation

HRID 847425 reaction equation
C(O[CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH2:17])[C:15](=[O:18])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=O)C.[NH2:19][N:20]1[C:25]([NH2:26])=[CH:24][C:23]([NH2:27])=[N:22][C:21]1=[S:28].CO.N>C(#N)C>[NH2:17][CH:16]1[C:15](=[O:18])[N:10]2[C:11]([C:12]([O-:14])=[O:13])=[C:6]([CH2:5][S:28][C:21]3[N:22]=[C:23]([NH2:27])[CH:24]=[C:25]([NH2:26])[N+:20]=3[NH2:19])[CH2:7][S:8][C@H:9]12

Participants

6

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 14918341,4,6-Triaminopyrimidine-2-thioneHCID 113463103-Acetoxymethyl-7-amino-3cephem-4-carboxylic acid

Product 1

HCID 677879807-Amino-3-(1,4,6-triaminopyrimidinium-2-yl)thiomethyl-3-cephem-4-carboxylateYield 72.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Under an anhydrous condition, a solution containing 2.72 g of 3-acetoxymethyl-7-amino-3-cephem-4-carboxylic acid and 1.50 g of 1,4,6-triamino-2(1H)-pyrimidinethione suspended in 20 ml of dry acetonitrile was cooled to 0° C.; and 4.8 ml of boron trifluoride diethylether was added. The temperature of the reaction solution was increased to 50° C; the solution was stirred for two hours; and then 10 ml of methyl alcohol was added. The resultant solution was stirred for 10 minutes and was added with 30 ml of ice water. The pH of the solution was adjusted to 7.1 by adding aqueous ammonia solution. After concentration under a reduced pressure, e.g., about 20 mmHg, the solution was adjusted to pH 3.7 with 2N-aqueous hydrochloric acid; and allowed to stand at a room temperature for 24 hrs. The precipitates resulted from the reaction solution were filtered, washed with 10 ml of distilled water and with 10 ml of methyl alcohol, and dried to give 2.55 g of the title compound as a solid.

Workup

  1. temperatureThe temperature of the reaction solution was increased to 50° C
  2. concentrationAfter concentration under a reduced pressure, e.g., about 20 mmHg
  3. waitto stand at a room temperature for 24 hrs
  4. customThe precipitates resulted from the reaction solution
  5. filtrationwere filtered
  6. washwashed with 10 ml of distilled water and with 10 ml of methyl alcohol
  7. customdried

Sources & evidence

ORD record
ord-ab2c39e6182849b18506c67b49451ab4
Source dataset
uspto-grants-1992_08
Patent number
US05142041

Reaction notes

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