Trifluoroacetic acid → HCID 178524523, compound

HRID 839020Notes

Reaction equation

HRID 839020 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 1 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-431cdb580bd14c29812ccf62f742e1bc
Source dataset
uspto-grants-1978_06
Patent number
US04093723

Reaction notes

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