Acetone → Benzhydryl 7-(2-thienylacetamido)-3-acetyl-2-cephem-4-carboxylate

HRID 596832Notes

Reaction equation

HRID 596832 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[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][CH:10]1[C:36](=[O:37])[N:12]2[CH:13]([C:20]([O:22][CH:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=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 70617653HCID 70617653, compound

Product 1

HCID 70636001Benzhydryl 7-(2-thienylacetamido)-3-acetyl-2-cephem-4-carboxylateYield 71.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of 2.98 g. of benzhydryl 7-(2-thienylacetamido)-3-(1-hydroxyethyl)-2-cephem-4-carboxylate in 200 ml. of acetone was added dropwise 2.83 ml. of a 2.26 molar chromic acid solution. The reaction mixture was allowed to stir at room temperature for ten minutes, after which time approximately 10 ml. of isopropanol was added. The reaction mixture was stirred for 5 minutes and then evaporated in vacuo to dryness. The residue was taken up in a mixture of ethyl acetate and water and transferred to a separatory funnel with the aid of ethyl acetate. The organic layer was separated and washed successively with brine (4X), sodium bicarbonate solution, water, 1N.HCl, and brine (2X) and then dried over anhydrous sodium sulfate. The residue obtained upon evaporation in vacuo of the solution thereby obtained was chromatographed on a silica gel column using a toluene-ethyl acetate gradient to provide 2.11 g. (71.2 percent) of the title product:

Workup

  1. stirringThe reaction mixture was stirred for 5 minutes
  2. customevaporated in vacuo to dryness
  3. additionThe residue was taken up in a mixture of ethyl acetate and water
  4. customtransferred to a separatory funnel with the aid of ethyl acetate
  5. customThe organic layer was separated
  6. washwashed successively with brine (4X), sodium bicarbonate solution, water, 1N
  7. dry with materialHCl, and brine (2X) and then dried over anhydrous sodium sulfate
  8. customThe residue obtained upon evaporation in vacuo of the solution
  9. customthereby obtained
  10. customwas chromatographed on a silica gel column
  11. customto provide 2.11 g

Sources & evidence

ORD record
ord-3e4771adabd64312a2f2d02b5ec512f8
Source dataset
uspto-grants-1977_03
Patent number
US04012380

Reaction notes

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