Hydrochloric Acid → 7-[alpha-(2,3-Dihydro-2-oxo-1H-benzimidazol-1-ylcarbonylamino)phenylacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acid

HRID 461229Notes

Reaction equation

HRID 461229 reaction equation
O.O.[NH2:3][CH:4]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:5]([NH:7][CH:8]1[C:23](=[O:24])[N:10]2[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH2:13][S:14][C@H:9]12)=[O:6].[O:31]=[C:32]1[N:36]([C:37](Cl)=[O:38])[C:35]2[CH:40]=[CH:41][CH:42]=[CH:43][C:34]=2[NH:33]1.Cl>C(#N)C>[O:31]=[C:32]1[N:36]([C:37]([NH:3][CH:4]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:5]([NH:7][CH:8]2[C:23](=[O:24])[N:10]3[C:11]([C:20]([OH:22])=[O:21])=[C:12]([CH2:15][O:16][C:17](=[O:19])[CH3:18])[CH2:13][S:14][C@H:9]23)=[O:6])=[O:38])[C:35]2[CH:40]=[CH:41][CH:42]=[CH:43][C:34]=2[NH:33]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 105840642,3-dihydro-2-oxo-1H-benzimidazol-1-ylcarbonyl chlorideHCID 1317109647-(alpha-Aminophenylacetamido)-3-acetoxymethyl-3-cephem-4-carboxylic acid dihydrate

Product 1

HCID 1317109637-[alpha-(2,3-Dihydro-2-oxo-1H-benzimidazol-1-ylcarbonylamino)phenylacetamido]-3-acetoxymethyl-3-cephem-4-carboxylic acidYield 102.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 15 ml. of dry acetonitrile were added 883 mg. (2 mmoles) of 7-(α-aminophenylacetamido)-3-acetoxymethyl-3-cephem-4-carboxylic acid dihydrate. The mixture was cooled, and 3.13 grams (14.4 mmoles) of N,O-bis-trimethylsilylacetamide were added. Solution was complete within two minutes. The resulting mixture then was stirred at room temperature, and 452 mg. (2.3 mmoles) of 2,3-dihydro-2-oxo-1H-benzimidazol-1-ylcarbonyl chloride were added, the temperature of the mixture rising from 25° C. to 28° C. Analysis of a sample of the reaction mixture after 30 minutes by thin-layer chromatography (TLC) indicated that reaction was complete. After two hours, the reaction mixture was slowly dropped into rapidly stirred ice water, the pH of the resulting suspension being 1.9. The pH was adjusted to 1.7 by addition of hydrochloric acid. The mixture was filtered, and the solid which was collected was washed with dilute hydrochloric acid and air-dried to give 1.16 grams of the title compound as a buff-colored powder.

Workup

  1. temperatureThe mixture was cooled
  2. customrising from 25° C. to 28° C
  3. customAnalysis of a sample of the reaction mixture after 30 minutes by thin-layer chromatography (TLC) indicated that reaction
  4. waitAfter two hours
  5. filtrationThe mixture was filtered
  6. customthe solid which was collected
  7. washwas washed with dilute hydrochloric acid
  8. customair-dried

Sources & evidence

ORD record
ord-c50655939eaa4a179f5d4919574927b1
Source dataset
uspto-grants-1977_12
Patent number
US04061861

Reaction notes

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