Dimethylformamide → HCID 131714983, compound

HRID 1248878Notes

Reaction equation

HRID 1248878 reaction equation
BrCC(N[CH:6]1[C:21](=[O:22])[N:8]2[C:9]([C:18]([OH:20])=[O:19])=[C:10]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[CH2:11][S:12][C@H:7]12)=O.[Cl:23][C:24]1[CH:37]=[CH:36][C:27]([O:28][CH2:29][C:30]2[O:31][C:32]([SH:35])=[N:33][N:34]=2)=[CH:26][CH:25]=1.C[N:39](C)[CH:40]=[O:41].[C:43](=O)([O-])[O-].[K+].[K+]>CCOCC>[Cl:23][C:24]1[CH:37]=[CH:36][C:27]([O:28][CH2:29][C:30]2[O:31][C:32]([S:35][CH:6]3[C:21](=[O:22])[N:8]4[C:9]([C:18]([OH:20])=[O:19])=[C:10]([CH2:13][NH:14][C:15](=[O:17])[CH3:16])[CH:11]([NH:39][C:40](=[O:41])[CH3:43])[S:12][C@H:7]34)=[N:33][N:34]=2)=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 70468832HCID 70468832, compoundHCID 178527967HCID 178527967, compound

Product 1

HCID 131714983HCID 131714983, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1.96 g. of 7-bromoacetylamino-3-acetylaminomethylceph-3-em-4-carboxylic acid and 1.45 g. of 2-(4-chlorophenoxymethyl)-5-mercapto-1,3,4-oxadiazole were dissolved in 20 ml. of anhydrous dimethyl formamide and 1.52 g. of calcinated potassium carbonate were added thereto. The reaction mixture was stirred at ambient temperature for 8 hours. 50 ml. of ether were added, the precipitate was filtered off and dissolved in 50 ml. of water. The pH of the solution was adjusted to 5 by adding some diluted sulphuric acid and then it was extracted with 30 ml. of ethyl acetate. The pH of the aqueous phase was adjusted to 2 by adding some diluted sulphuric acid and the mixture was extracted with 60 ml. of ethyl acetate. The organic extract was dried over magnesium sulphate. The solvent was evaporated in vacuo and the residue was treated with ether. Thus 2.07 g. of 7-[2-(4-chlorophenoxymethyl)-1,3,4-oxadiazole-5-ylthio]-acetamido-3-acetylaminomethylceph-3-em-4-carboxylic acid were obtained.

Workup

  1. filtrationthe precipitate was filtered off
  2. dissolutiondissolved in 50 ml
  3. additionby adding some diluted sulphuric acid
  4. extractionit was extracted with 30 ml
  5. additionby adding some diluted sulphuric acid
  6. extractionthe mixture was extracted with 60 ml
  7. extractionThe organic extract
  8. dry with materialwas dried over magnesium sulphate
  9. customThe solvent was evaporated in vacuo
  10. additionthe residue was treated with ether

Sources & evidence

ORD record
ord-d475c64e19ba4838aa94602c319bc08f
Source dataset
uspto-grants-1986_12
Patent number
US04626533

Reaction notes

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