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Sodium Iodide → Benzhydryl 7beta-[2-difluoromethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate chloride

HRID 1614084
Notes
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Reaction equation

HRID 1614084 reaction equation
[F:1][CH:2]([F:61])[O:3][N:4]=[C:5]([C:36]1[N:37]=[C:38]([NH:41][C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[S:39][CH:40]=1)[C:6]([NH:8][C@@H:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16][Cl:17])[CH2:14][S:15][C@H:10]12)=[O:7].[CH3:62][N:63]1[CH:67]=[CH:66][CH:65]=[N:64]1.[I-].[Na+]>CC(C)=O>[Cl-:17].[F:1][CH:2]([F:61])[O:3][N:4]=[C:5]([C:36]1[N:37]=[C:38]([NH:41][C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[S:39][CH:40]=1)[C:6]([NH:8][C@@H:9]1[C:34](=[O:35])[N:11]2[C:12]([C:18]([O:20][CH:21]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])=[C:13]([CH2:16][N+:64]3[N:63]([CH3:62])[CH:67]=[CH:66][CH:65]=3)[CH2:14][S:15][C@H:10]12)=[O:7]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 702551H-Pyrazole, 1-methyl-HCID 131716601Benzhydryl 7beta-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 178480375Benzhydryl 7beta-[2-difluoromethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate chlorideYield 83.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of benzhydryl 7β-[2-difluoromethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-chloromethyl-3-cephem-4-carboxylate (syn isomer, 8.76 g), N-methylpyrazole (8.76 g), sodium iodide (1.5 g) and acetone (9 ml) was stirred at ambient temperature for 19 hours. The reaction mixture was evaporated, and ethyl acetate (200 ml) and 5% aqueous solution of sodium thiosulfate were added to the residue. The organic layer was separated and tetrahydrofuran (100 ml) was added thereto. The solution was dried over magnesium sulfate and evaporated and the residue was dissolved in a mixture of tetrahydrofuran (200 ml) and water (65 ml). The solution was subjected to column chromatography on an ion-exchange resin "Amberlite IRA-400"(Cl⃝ form), and eluted with a mixture of tetrahydrofuran and water (15:1 V/V). The fractions containing the object compound were collected, combined and evaporated. The residue was triturated with diisopropyl ether to give benzhydryl 7β-[2-difluoromethoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-(2-methyl-1-pyrazolio)methyl-3-cephem-4-carboxylate chloride (syn isomer, 8.0 g).

Workup

  1. customThe reaction mixture was evaporated
  2. additionethyl acetate (200 ml) and 5% aqueous solution of sodium thiosulfate were added to the residue
  3. customThe organic layer was separated
  4. additiontetrahydrofuran (100 ml) was added
  5. dry with materialThe solution was dried over magnesium sulfate
  6. customevaporated
  7. dissolutionthe residue was dissolved in a mixture of tetrahydrofuran (200 ml) and water (65 ml)
  8. washeluted with a mixture of tetrahydrofuran and water (15:1 V/V)
  9. additionThe fractions containing the object compound
  10. customwere collected
  11. customevaporated
  12. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-f76182323e8d49278ecd050cdbb6451f
Source dataset
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05194432

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes