Sodium Iodide → HCID 131712707, compound

HRID 434871Notes

Reaction equation

HRID 434871 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:45]1[N:46]=[C:47]([NH:50][CH:51]=[O:52])[S:48][CH:49]=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].[I-].[Na+].FC(F)(F)C(OC(=O)C(F)(F)F)=O>O1CCCC1.CC(C)=O>[CH3:1][O:2][N:3]=[C:4]([C:45]1[N:46]=[C:47]([NH:50][CH:51]=[O:52])[S:48][CH:49]=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:38]=[CH:39][CH:40]=[CH:41][CH:42]=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][C@H:9]12)=[O:6]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 9845Trifluoroacetic anhydrideHCID 131713052HCID 131713052, compound

Product 1

HCID 131712707HCID 131712707, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a solution of benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-methyl-1-piperazinyl)carbonyloxymethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (1.5 g) in a mixture of tetrahydrofuran (30 ml) and acetone (15 ml) was dissolved sodium iodide (1.44 g) under ice-cooling and thereto was at a time added trifluoroacetic anhydride (2.04 ml) followed by stirring for 2.5 hours. The reaction mixture was evaporated and to the residue were added ethyl acetate and water. The ethyl acetate layer was separated, washed with 5% aqueous solution of sodium thiosulfate, and an aqueous solution of sodium chloride, dried over magnesium sulfate, treated with activated charcoal and then evaporated to give benzhydryl 7-[2-methoxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-methyl-1-piperazinyl)carbonyloxymethyl-3-cephem-4-carboxylate.trifluoroacetate (syn isomer) (1.5 g).

Workup

  1. temperaturecooling
  2. customThe reaction mixture was evaporated and to the residue
  3. additionwere added ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. washwashed with 5% aqueous solution of sodium thiosulfate
  6. dry with materialan aqueous solution of sodium chloride, dried over magnesium sulfate
  7. additiontreated with activated charcoal
  8. customevaporated

Sources & evidence

ORD record
ord-c919cf5cb23645aab9d5c05628ba152a
Source dataset
uspto-grants-1983_08
Patent number
US04399278

Reaction notes

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