Trifluoroacetic acid → HCID 178524523, compound

HRID 237159Notes

Reaction equation

HRID 237159 reaction equation
[Na+:1].[Na+].C([O:7][C:8]([CH:10]([C:38]1[S:39][CH:40]=[CH:41][CH:42]=1)[C:11]([NH:13][CH:14]1[C:36](=[O:37])[N:16]2[C:17]([C:33]([O-:35])=[O:34])=[C:18]([CH:21]([S:27][C:28]3[NH:32][N:31]=[N:30][N:29]=3)[CH2:22][S:23]([OH:26])(=[O:25])=[O:24])[CH2:19][S:20][C@H:15]12)=[O:12])=[O:9])(C)(C)C.C([O:47][C:48]([CH:50]([C:78]1[S:79][CH:80]=[CH:81][CH:82]=1)[C:51]([NH:53][CH:54]1[C:76](=[O:77])[N:56]2[C:57]([C:73]([O-:75])=[O:74])=[C:58]([CH:61]([S:67][C:68]3[NH:72][N:71]=[N:70][N:69]=3)[CH2:62][S:63]([OH:66])(=[O:65])=[O:64])[CH2:59][S:60][C@H:55]12)=[O:52])=[O:49])(C)(C)C.FC(F)(F)C(O)=O.COC1C=CC=C(OC)C=1>>[Na+:1].[Na+:1].[Na+:1].[C:8]([CH:10]([C:38]1[S:39][CH:40]=[CH:41][CH:42]=1)[C:11]([NH:13][CH:14]1[C:36](=[O:37])[N:16]2[C:17]([C:33]([O-:35])=[O:34])=[C:18]([CH:21]([S:27][C:28]3[NH:29][N:30]=[N:31][N:32]=3)[CH2:22][S:23]([OH:26])(=[O:25])=[O:24])[CH2:19][S:20][C@H:15]12)=[O:12])([OH:9])=[O:7].[C:48]([CH:50]([C:78]1[S:79][CH:80]=[CH:81][CH:82]=1)[C:51]([NH:53][CH:54]1[C:76](=[O:77])[N:56]2[C:57]([C:73]([O-:75])=[O:74])=[C:58]([CH:61]([S:67][C:68]3[NH:69][N:70]=[N:71][N:72]=3)[CH2:62][S:63]([OH:66])(=[O:65])=[O:64])[CH2:59][S:60][C@H:55]12)=[O:52])([OH:49])=[O:47].[C:8]([CH:10]([C:38]1[S:39][CH:40]=[CH:41][CH:42]=1)[C:11]([NH:13][CH:14]1[C:36](=[O:37])[N:16]2[C:17]([C:33]([O-:35])=[O:34])=[C:18]([CH:21]([S:27][C:28]3[NH:29][N:30]=[N:31][N:32]=3)[CH2:22][S:23]([OH:26])(=[O:25])=[O:24])[CH2:19][S:20][C@H:15]12)=[O:12])([OH:9])=[O:7]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90251,3-DimethoxybenzeneHCID 178451132HCID 178451132, compound

Product 1

HCID 178524523HCID 178524523, compound

Procedure

7-(α-t-Butoxycarbonyl-2-thienylacetamido)-3-(1-sulfomethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid disodium salt (1.0 g.) is stirred in a mixture of 10 ml. of trifluoroacetic acid and 10 ml. of m-dimethoxybenzene at 25° for one hour. The mixture is evaporated to dryness and the residue is triturated with ether. The precipitated product is collected by filtration and dissolved in methanol. A sodium methoxide solution is added until pH 7.0, the mixture is diluted with ether and the product is dissolved in water and lyophilized to give 7-(α-carboxy-2-thienylacetamido)-3-(1-sulfomethyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylic acid trisodium salt.

Workup

  1. customThe mixture is evaporated to dryness
  2. customthe residue is triturated with ether
  3. filtrationThe precipitated product is collected by filtration
  4. dissolutiondissolved in methanol
  5. additionA sodium methoxide solution is added until pH 7.0
  6. additionthe mixture is diluted with ether
  7. dissolutionthe product is dissolved in water

Sources & evidence

ORD record
ord-0d3fa8a29cef45f9888654d75d709649
Source dataset
uspto-grants-1979_06
Patent number
US04159373

Reaction notes

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