Acetone → HCID 12302618, compound

HRID 2286270Notes

Reaction equation

HRID 2286270 reaction equation
[NH2:1][CH:2]1[C:23](=[O:24])[N:4]2[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH2:9][S:10][C:11]3[NH:12]C4C=CC=CC=4N=3)[CH2:7][S:8][C@H:3]12.O.[NH:26]1[C:30](CC(O)=O)=[N:29][N:28]=[N:27]1.Cl.[CH3:36][C:37](C)=[O:38]>>[N:29]1([CH2:36][C:37]([NH:1][CH:2]2[C:23](=[O:24])[N:4]3[C:5]([C:20]([OH:22])=[O:21])=[C:6]([CH2:9][S:10][C:11]4[S:8][C:3]([CH3:2])=[N:4][N:12]=4)[CH2:7][S:8][C@H:3]23)=[O:38])[CH:30]=[N:26][N:27]=[N:28]1

Participants

6

Reactant 5

HCID 180Acetone2×HCID 313Hydrochloric Acid2×HCID 962WaterHCID 12877738HCID 12877738, compoundHCID 178525261HCID 178525261, compound

Product 1

HCID 12302618HCID 12302618, compound

Conditions

Temperature
60 °C

Procedure

Into a 5-liter three-necked flask provided with a thermometer, were charged 362 mg of 7-amino-3-(benzimidazol-2-yl)thiomethyl-3-cephem-4-carboxylic acid, 900 ml of acetone, and 1 liter of water to form a solution. After adding a solution of 290 mg of 2-methyl-1,3,4-thiadiazol-5-ylthio ester of 1H-tetrazoleacetic acid in 100 ml of acetone, the solution was heated to 60° C., further admixed with 2 ml of 0.5 N aqueous hydrochloric acid, and the reaction was allowed to proceed for 4 hours. On analysis of the reaction solution by high speed liquid chromatography, the conversion was found to be 66%. After cooling, pH was decreased with 1 N hydrochloric acid, and the reaction solution was subjected to separation and purification with a synthetic adsorbent column in a customary way to obtain 273.6 mg of 7-(1H-tetrazol-1-ylacetamido)-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid as a white powder (93% purity).

Workup

  1. customInto a 5-liter three-necked flask provided with a thermometer
  2. customto form a solution
  3. temperatureAfter cooling
  4. customthe reaction solution was subjected to separation and purification with a synthetic adsorbent column in a customary way

Sources & evidence

ORD record
ord-2f35e19617254ba9b7a102321bae9112
Source dataset
uspto-grants-1982_04
Patent number
US04327211

Reaction notes

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