Water → Jones' reagent

HRID 1278106Notes

Reaction equation

HRID 1278106 reaction equation
[CH3:1][O:2][N:3]=[C:4]([C:22]1[N:23]=[C:24]([NH:27][C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])[S:25][CH:26]=1)[C:5]([NH:7][CH:8]1[C:20](=[O:21])[N:10]2[C:11]([C:17]([OH:19])=[O:18])=[C:12]([CH2:15][OH:16])[CH2:13][S:14][C@H:9]12)=[O:6].[S:34](=[O:38])(=[O:37])([OH:36])[OH:35].[O-2:39].[O-2:40].[O-2:41].[Cr+6:42].O>CN(C)C=O.CC(C)=O>[CH3:5][C:4]([CH3:22])=[O:39].[OH:37][S:34]([OH:38])(=[O:36])=[O:35].[O:39]=[Cr:42](=[O:41])=[O:40].[CH3:1][O:2][N:3]=[C:4]([C:22]1[N:23]=[C:24]([NH:27][C:28](=[O:33])[C:29]([F:31])([F:32])[F:30])[S:25][CH:26]=1)[C:5]([NH:7][CH:8]1[C:20](=[O:21])[N:10]2[C:11]([C:17]([OH:19])=[O:18])=[C:12]([CH:15]=[O:16])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

8

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 10219390chromium (VI) trioxideHCID 131711624HCID 131711624, compound

Product 2

HCID 131709961Jones' reagentHCID 131711623HCID 131711623, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

7-[2-Methoxyimino-2-{2-(2,2,2-trifluoroacetamido)-1,3-thiazol-4-yl}acetamido]-3-hydroxymethyl-3-cephem-4-carboxylic acid (syn isomer) (1.0 g.) was dissolved in a mixture of dimethylformamide (6 ml.) and acetone (30 ml.). Jones reagent (1.25 ml.), which was prepared from conc. sulfuric acid (0.28 ml.), chromium trioxide (0.33 g.) and water (0.9 ml.), was dropwise added thereto over 2 minutes with stirring and cooling at 0° to 2° C. After stirring for 20 minutes at the same temperature, the reaction mixture was poured into ice-water (50 ml.). After acetone was distilled off, the residue was twice extracted with ethyl acetate (50 ml.). The extracts were washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solvent was distilled off and the residue was pulverized with diisopropyl ether to give 7-[2-methoxyimino-2-{2-(2,2,2-trifluoroacetamido)-1,3-thiazol-4-yl}-acetamido]-3-formyl-3-cephem-4-carboxylic acid (syn isomer) [or this compound can be represented as 3-hydroxy-6-[2-methoxyimino-2-{2-(2,2,2-trifluoroacetamido)-1,3-thiazol-4-yl}acetamido]-5a, 6-dihydro-3H,7H-azeto[2,1-b]furo[3,4-d][1,3]thiazine-1,7(4H)dione (syn isomer)] (0.56 g.).

Workup

  1. additionwas dropwise added
  2. temperaturecooling at 0° to 2° C
  3. stirringAfter stirring for 20 minutes at the same temperature
  4. distillationAfter acetone was distilled off
  5. extractionthe residue was twice extracted with ethyl acetate (50 ml.)
  6. washThe extracts were washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-c530304f601d4e70a60e8bb2676cc55f
Source dataset
uspto-grants-1981_07
Patent number
US04279818

Reaction notes

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