Ethyl Acetate → HCID 70505301, compound

HRID 1463139Notes

Reaction equation

HRID 1463139 reaction equation
P(Cl)(Cl)Cl.[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][C:11]([NH:13][CH:14]1[C:47](=[O:48])[N:16]2[C:17]([C:31]([O:33][CH:34]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:32])=[C:18]([CH2:23][S:24][C:25]3[N:29]([CH3:30])[N:28]=[N:27][N:26]=3)[C@@H:19]([CH3:22])[S:20](=O)[C@H:15]12)=[O:12].CCOC(C)=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[S:5]1[CH:9]=[CH:8][CH:7]=[C:6]1[CH2:10][C:11]([NH:13][CH:14]1[C:47](=[O:48])[N:16]2[C:17]([C:31]([O:33][CH:34]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:32])=[C:18]([CH2:23][S:24][C:25]3[N:29]([CH3:30])[N:28]=[N:27][N:26]=3)[C@@H:19]([CH3:22])[S:20][C@H:15]12)=[O:12]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24387Phosphorus trichlorideHCID 516892Sodium BicarbonateHCID 70505391HCID 70505391, compound

Product 1

HCID 70505301HCID 70505301, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 0.38 ml portion of PCl3 was added to a solution of 326 mg of diphenylmethyl 7-(2-thienylacetamido)-2α-methyl-3-(1-methyl-1H-tetrazol-5-yl)thiomethylceph-3-em-4-carboxylate 1-oxide in 5 ml of DMF at -10° C., followed by stirring at the same temperature for 15 minutes. AcOEt and 5% aqueous NaHCO3 solution were added to the reaction solution to separate out the AcOEt layer. The AcOEt layer was washed with saturated aqueous NaCl solution and dried over Na2SO4, followed by distilling off the AcOEt under reduced pressure. The residue was added on a column of silica gel, and the fractions eluted with CH2Cl2.AcOEt (25:1) were collected, followed by distilling off the solvent under reduced pressure, thus yielding 225 mg (71%) of diphenylmethyl 7-(2-thienylacetamido)-2α-methyl-3-(1-methyl-1H-tetrazol-5-yl)thiomethylceph-3-em-4-carboxylate.

Workup

  1. customto separate out the AcOEt layer
  2. washThe AcOEt layer was washed with saturated aqueous NaCl solution
  3. dry with materialdried over Na2SO4
  4. distillationby distilling off the AcOEt under reduced pressure
  5. additionThe residue was added on a column of silica gel
  6. washthe fractions eluted with CH2Cl2
  7. customAcOEt (25:1) were collected
  8. distillationby distilling off the solvent under reduced pressure

Sources & evidence

ORD record
ord-c455ee00e2e74e54a120d4fb5b69838e
Source dataset
uspto-grants-1984_07
Patent number
US04463172

Reaction notes

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