Jones' reagent → HCID 131714353, compound

HRID 464207Notes

Reaction equation

HRID 464207 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH:14]([NH:16][C:17]1[S:18][CH:19]=[C:20]([C:22](=[N:53][O:54][CH3:55])[C:23]([NH:25][CH:26]2[C:51](=[O:52])[N:28]3[C:29]([C:35]([O:37][CH:38]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:36])=[C:30]([CH2:33][OH:34])[CH2:31][S:32][C@H:27]23)=[O:24])[N:21]=1)=[O:15]>CC(C)=O>[CH:14]([NH:16][C:17]1[S:18][CH:19]=[C:20]([C:22](=[N:53][O:54][CH3:55])[C:23]([NH:25][CH:26]2[C:51](=[O:52])[N:28]3[C:29]([C:35]([O:37][CH:38]([C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)[C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:36])=[C:30]([CH:33]=[O:34])[CH2:31][S:32][C@H:27]23)=[O:24])[N:21]=1)=[O:15]

Participants

4

Reactant 2

HCID 131709961Jones' reagentHCID 131714354HCID 131714354, compound

Product 1

HCID 131714353HCID 131714353, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones reagent (14.5 ml) was dropwise added to a suspension of benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-hydroxymethyl-3-cephem-4-carboxylate (syn isomer) (19.5 g) in acetone (300 ml) at 0° to 3° C. under stirring and the mixture was stirred for 20 minutes at the same temperature. The reaction mixture was filtered and the filtrate was washed with acetone. To the mixture of the filtrate and washings was added ethyl acetate (300 ml) and washed with brine and dried over magnesium sulfate. The solution was evaporated and the residue was pulverized in diethyl ether to give benzhydryl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-formyl-3-cephem-4-carboxylate (syn isomer) (13.7 g).

Workup

  1. stirringthe mixture was stirred for 20 minutes at the same temperature
  2. filtrationThe reaction mixture was filtered
  3. washthe filtrate was washed with acetone
  4. additionTo the mixture of the filtrate and washings
  5. additionwas added ethyl acetate (300 ml)
  6. washwashed with brine
  7. dry with materialdried over magnesium sulfate
  8. customThe solution was evaporated

Sources & evidence

ORD record
ord-a1b6d1d2d5434b3aaa843a5a8e80695b
Source dataset
uspto-grants-1985_10
Patent number
US04546101

Reaction notes

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