Acetone → Benzhydryl 7-[2-methoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(4-methyl-1-piperazinyl)carbonyloxymethyl-3-cephem-4-carboxylate

HRID 434872Notes

Reaction equation

HRID 434872 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:45]1[N:49]=[C:48]([NH2:50])[S:47][N:46]=1)[C:5]([NH:7][CH:8]1[C:43](=[O:44])[N:10]2[C:11]([C:27]([O:29][CH:30]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])=[C:12]([CH2:16][O:17][C:18]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)=[O:19])[CH2:13][S:14](=O)[C@H:9]12)=[O:6].CC(C)=O.[I-].[Na+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1>[CH3:1][O:2][N:3]=[C:4]([C:45]1[N:49]=[C:48]([NH2:50])[S:47][N:46]=1)[C:5]([NH:7][CH:8]1[C:43](=[O:44])[N:10]2[C:11]([C:27]([O:29][CH:30]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[O:28])=[C:12]([CH2:16][O:17][C:18]([N:20]3[CH2:25][CH2:24][N:23]([CH3:26])[CH2:22][CH2:21]3)=[O:19])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

6

Reactant 4

HCID 180AcetoneHCID 5238Sodium IodideHCID 9845Trifluoroacetic anhydrideHCID 131712704Benzhydryl 7-[2-methoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(4-methyl-1-piperazinyl)carbonyloxymethyl-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 131712705Benzhydryl 7-[2-methoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(4-methyl-1-piperazinyl)carbonyloxymethyl-3-cephem-4-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzhydryl 7-[2-methoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(4-methyl-1-piperazinyl)carbonyloxymethyl-3-cephem-4-carboxylate-1-oxide (syn isomer)(1.25 g) in a mixture of dry acetone (150 ml) and tetrahydrofuran (50 ml) was stirred under ice-water cooling and thereto were added sodium iodide (620 mg) and trifluoroacetic anhydride (0.59 ml) followed by stirring for 4 hours at the same temperature. The reaction mixture was evaporated under reduced pressure and to the residue were added ethyl acetate (60 ml) and water (20 ml). The ethyl acetate layer was separated therefrom, washed with 5% aqueous solution of sodium thiosulfate (20 ml×3), and a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, treated with activated charcoal and then evaporated under reduced pressure. The residue was washed with diethyl ether and dried to give benzhydryl 7-[2-methoxyimino-2-(5-amino-1,2,4-thiadiazol-3-yl)acetamido]-3-(4-methyl-1-piperazinyl)carbonyloxymethyl-3-cephem-4-carboxylate.ditrifluoroacetate (syn isomer)(0.9 g).

Workup

  1. stirringby stirring for 4 hours at the same temperature
  2. customThe reaction mixture was evaporated under reduced pressure and to the residue
  3. additionwere added ethyl acetate (60 ml) and water (20 ml)
  4. customThe ethyl acetate layer was separated
  5. washwashed with 5% aqueous solution of sodium thiosulfate (20 ml×3)
  6. dry with materiala saturated aqueous solution of sodium chloride, dried over magnesium sulfate
  7. additiontreated with activated charcoal
  8. customevaporated under reduced pressure
  9. washThe residue was washed with diethyl ether
  10. customdried

Sources & evidence

ORD record
ord-3caaed4844244114b6f8629face0a542
Source dataset
uspto-grants-1983_08
Patent number
US04399278

Reaction notes

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