Ethyl Acetate → HCID 131716560, compound

HRID 1032228Notes

Reaction equation

HRID 1032228 reaction equation
[NH2:1][CH:2]1[C:27](=[O:28])[N:4]2[C:5]([C:24]([OH:26])=[O:25])=[C:6]([CH2:9][S:10][C:11]3[N:16]4[N:17]=[C:18]([CH2:20][O:21][CH3:22])[N:19]=[C:15]4[N:14]=[C:13]([CH3:23])[CH:12]=3)[CH2:7][S:8][C@H:3]12.N12CCCCC1C=NCCC2.[C:40]([O:46][CH2:47]I)(=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42].C(OCC)(=O)C>CC(C)=O.CCOCC.O>[NH2:1][CH:2]1[C:27](=[O:28])[N:4]2[C:5]([C:24]([O:26][CH2:47][O:46][C:40](=[O:45])[C:41]([CH3:44])([CH3:43])[CH3:42])=[O:25])=[C:6]([CH2:9][S:10][C:11]3[N:16]4[N:17]=[C:18]([CH2:20][O:21][CH3:22])[N:19]=[C:15]4[N:14]=[C:13]([CH3:23])[CH:12]=3)[CH2:7][S:8][C@H:3]12

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 104401Iodomethyl pivalateHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 131716544HCID 131716544, compound

Product 1

HCID 131716560HCID 131716560, compoundYield 47.4%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

In 80 ml of acetone was suspended 16.9 g of 7-amino-3-[(2-methoxymethyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7yl)thiomethyl]-3-cephem-4-carboxylic acid and ice-cooled, and then 5.98 ml of 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU) was added dropwise to the solution and the mixture was stirred for 30 minutes. After 9.68 g of pivaloyloxymethyl iodide was added dropwise to the mixture, the mixture was stirred at room temperature for 20 minutes. After the reaction mixture was poured into a mixed solution of 280 ml of ethyl acetate and 200 ml of water and stirred, an organic layer was separated therefrom, washed with water, further washed with a saturated saline solution and dried over anhydrous magnesium sulfate. By removing a solvent, an oily product was obtained. This oily product was purified through silica gel column chromatography. To the oily product obtained was added ether to powderize, and it was collected by filtration and dried to obtain 10.17 g of the title compound.

Workup

  1. temperaturecooled
  2. stirringthe mixture was stirred at room temperature for 20 minutes
  3. stirringstirred
  4. customan organic layer was separated
  5. washwashed with water
  6. washfurther washed with a saturated saline solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customBy removing a solvent
  9. customan oily product was obtained
  10. customThis oily product was purified through silica gel column chromatography
  11. customTo the oily product obtained
  12. filtrationit was collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-b93fe695a5c649cdb2d9720beaf6cbaf
Source dataset
uspto-grants-1990_09
Patent number
US04956462

Reaction notes

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