Trifluoroacetic acid → HCID 88683627, compound

HRID 1164430Notes

Reaction equation

HRID 1164430 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([N:30]([O:42][CH3:43])[C:31](=[O:41])[CH2:32][C:33]3[N:34]=[C:35]([NH:38][CH:39]=[O:40])[S:36][CH:37]=3)[C:28](=[O:44])[N:10]2[C:11]=1[C:12]([O:14]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13])(=[O:3])[CH3:2].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:29]([N:30]([O:42][CH3:43])[C:31](=[O:41])[CH2:32][C:33]3[N:34]=[C:35]([NH:38][CH:39]=[O:40])[S:36][CH:37]=3)[C:28](=[O:44])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 88684568HCID 88684568, compound

Product 1

HCID 88683627HCID 88683627, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (10 ml) is dissolved diphenylmethyl 3-acetoxymethyl-7-[N-methoxy-2-(2-formylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylate (535 mg). Under ice-cooling, anisole (1 ml) and trifluoroacetic acid (1.5 ml) are added and the mixture is stirred for 1.5 hours. The reaction mixture is concentrated under reduced pressure and the residue is dissolved in ethyl acetate and extracted with a dilute aqueous solution of sodium hydrogen carbonate. The water layer is adjusted to pH 1 with dil HCl and extracted with ethyl acetate. The extract is washed with aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue is washed with isopropyl ether to give a powder of 3-acetoxymethyl-7-[N-methoxy-2-(2-formylamino-1,3-thiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (390 mg).

Workup

  1. temperatureUnder ice-cooling
  2. concentrationThe reaction mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in ethyl acetate
  4. extractionextracted with a dilute aqueous solution of sodium hydrogen carbonate
  5. extractionextracted with ethyl acetate
  6. washThe extract is washed with aqueous sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. washThe residue is washed with isopropyl ether

Sources & evidence

ORD record
ord-f3c916b1be5f4fd6bdfe15f56b9bc793
Source dataset
uspto-grants-1983_01
Patent number
US04369312

Reaction notes

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