Trifluoroacetic acid → 3-Methoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid

HRID 972493Notes

Reaction equation

HRID 972493 reaction equation
C1(C([O:14][C:15]([C:17]2[N:22]3[C:23](=[O:34])[CH:24]([NH:25][C:26](=[O:33])[CH2:27][C:28]4[S:29][CH:30]=[CH:31][CH:32]=4)[C@H:21]3[S:20][CH2:19][C:18]=2[CH:35]=[N:36][O:37][CH3:38])=[O:16])C2C=CC=CC=2)C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:38][O:37][N:36]=[CH:35][C:18]1[CH2:19][S:20][C@@H:21]2[CH:24]([NH:25][C:26](=[O:33])[CH2:27][C:28]3[S:29][CH:30]=[CH:31][CH:32]=3)[C:23](=[O:34])[N:22]2[C:17]=1[C:15]([OH:16])=[O:14]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131710499Diphenylmethyl 3-methoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate

Product 1

HCID 1317104973-Methoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acidYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diphenylmethyl-3-methoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylate (394 mg) in methylene chloride (11 ml) are added anisole (1.1 ml) and trifluoroacetic acid (1.1 ml) at 0° C. under argon atmosphere, and the mixture is kept at the same temperature for 25 minutes, and at room temperature for 25 minutes. The reaction mixture is evaporated, and trituration of the residue in ether gives 3-methoxyiminomethyl-7-(2-thienylacetamido)-3-cephem-4-carboxylic acid (216 mg). m.p. 186°-189° C.

Workup

  1. waitat room temperature for 25 minutes
  2. customThe reaction mixture is evaporated

Sources & evidence

ORD record
ord-20312fa829b8457f9345efd1b4bca639
Source dataset
uspto-grants-1977_10
Patent number
US04053469

Reaction notes

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