Sodium Iodide → Benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-iodomethyl-3-cephem-4-carboxylate-1-oxide

HRID 34504Notes

Reaction equation

HRID 34504 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:58][O:59][CH:60]([F:62])[F:61])[C:27]([NH:29][CH:30]2[C:56](=[O:57])[N:32]3[C:33]([C:40]([O:42][CH:43]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:41])=[C:34]([CH2:38]Cl)[CH2:35][S:36](=[O:37])[C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-:63].[Na+]>CC(C)=O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:58][O:59][CH:60]([F:62])[F:61])[C:27]([NH:29][CH:30]2[C:56](=[O:57])[N:32]3[C:33]([C:40]([O:42][CH:43]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=4)=[O:41])=[C:34]([CH2:38][I:63])[CH2:35][S:36](=[O:37])[C@H:31]23)=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 131715684Benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide

Product 1

HCID 131715683Benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-iodomethyl-3-cephem-4-carboxylate-1-oxideYield 42.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-chloromethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (29 g), sodium iodide (14.6 g) and acetone (300 ml) was stirred for 2.0 hours at 0°-5° C. and evaporated. To the residue were added ethyl acetate (400 ml) and water (300 ml), and the organic layer was separated, dried and evaporated. The residue was subjected to column chromatography on silica gel (600 g) and the elution was carried out with a mixture of chloroform and ethyl acetate (15:1). The fractions containing the object compound were combined and evaporated. The residue was triturated with diisopropyl ether to give benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-iodomethyl-3-cephem-4-carboxylate-1-oxide (syn isomer) (13.57 g).

Workup

  1. customevaporated
  2. additionTo the residue were added ethyl acetate (400 ml) and water (300 ml)
  3. customthe organic layer was separated
  4. customdried
  5. customevaporated
  6. washthe elution
  7. additionwas carried out with a mixture of chloroform and ethyl acetate (15:1)
  8. additionThe fractions containing the object compound
  9. customevaporated
  10. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-13133262384848ee8f46663f1faf4e80
Source dataset
uspto-grants-1988_08
Patent number
US04761410

Reaction notes

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