Acetone → HCID 131710680, compound

HRID 596848Notes

Reaction equation

HRID 596848 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1([O:38][CH3:39])[C:36](=[O:37])[N:12]2[CH:13]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:21])[C:14]([CH:17]([OH:19])[CH3:18])=[CH:15][S:16][C@H:11]12)=[O:8].CC(C)=O.[Cr](O)(O)(=O)=O>C(O)(C)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][C:10]1([O:38][CH3:39])[C:36](=[O:37])[N:12]2[CH:13]([C:20]([O:22][CH:23]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)=[O:21])[C:14]([C:17](=[O:19])[CH3:18])=[CH:15][S:16][C@H:11]12)=[O:8]

Participants

5

Reactant 3

HCID 180AcetoneHCID 24425Chromic AcidHCID 70636076HCID 70636076, compound

Product 1

HCID 131710680HCID 131710680, compoundYield 47.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 0.154 g. of benzhydryl 7-(2-thienylacetamido)-7-methoxy-3-(1-hydroxyethyl)-2-cephem-4-carboxylate in 40 ml. of acetone was added 1.5 eq. of chromic acid. After stirring the mixture at room temperature for 10 minutes, 2 ml. of isopropanol was added. After stirring for an additional 5 minutes, the reaction mixture was evaporated in vacuo to dryness. The residue was dissolved in an ethyl acetate/water slurry. The organic layer was separated, washed successively with water (2X), aqueous sodium bicarbonate solution, 1N.HCl, and brine and dried over anhydrous sodium sulfate. Evaporation in vacuo to dryness provided product which was chromatographed on 5.0 g. of silica gel using a toluene-ethyl acetate gradient to give 0.073 g. (47.8 percent) of the title product as a white froth:

Workup

  1. stirringAfter stirring for an additional 5 minutes
  2. customthe reaction mixture was evaporated in vacuo to dryness
  3. dissolutionThe residue was dissolved in an ethyl acetate/water slurry
  4. customThe organic layer was separated
  5. washwashed successively with water (2X), aqueous sodium bicarbonate solution, 1N
  6. dry with materialHCl, and brine and dried over anhydrous sodium sulfate
  7. customEvaporation in vacuo to dryness
  8. customprovided product which
  9. customwas chromatographed on 5.0 g
  10. customof silica gel using a toluene-ethyl acetate gradient to give 0.073 g

Sources & evidence

ORD record
ord-c82a62e26b6c4344a6098b3f2ae10c7e
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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