Trifluoroacetic acid → 7beta-D-mandelamido-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid

HRID 1707472Notes

Reaction equation

HRID 1707472 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:36])[C@@H:24]([NH:25][C:26](=[O:35])[C@@H:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[OH:28])[C@H:21]3[S:20][CH2:19][C:18]=2[S:37][CH:38](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[S:39][C:40]2[N:41]=[N:42][NH:43][CH:44]=2)=[O:16])C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1.ClCCl.CO>[C:26]([NH:25][C@@H:24]1[C:23](=[O:36])[N:22]2[C:17]([C:15]([OH:16])=[O:14])=[C:18]([S:37][CH2:38][S:39][C:40]3[N:41]=[N:42][NH:43][CH:44]=3)[CH2:19][S:20][C@H:21]12)(=[O:35])[C@@H:27]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[OH:28]

Participants

6

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178525025HCID 178525025, compound

Product 1

HCID 1785248387beta-D-mandelamido-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acidYield 25%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

To a solution of 7β-D-mandelamido-3-(trityl-1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (445 mg: 0.502 mMol.) in a mixture of anisole (0.8 ml) and dichloromethane (2 ml) under ice cooling is added trifluoroacetic acid (2 ml), and the mixture is stirred under ice cooling for 30 minutes and at room temperature for 20 minutes. The reaction mixture is diluted with methanol (10 ml) and concentrated. The residue is dissolved in dilute aqueous sodium hydrogen carbonate water, washed with ethyl acetate, acidified with 10% hydrochloric acid, and extracted with ethyl acetate. The extract is dried over sodium sulfate and concentrated. The residue is pulverized with ether to give 7β-D-mandelamido-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid (59.2 mg) as yellowish white powder. Yield: 25%.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue is dissolved in dilute aqueous sodium hydrogen carbonate water
  3. washwashed with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract is dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bf0bff8efab048d0bc0f5657d35ba10c
Source dataset
uspto-grants-1994_10
Patent number
US05352792

Reaction notes

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