Tetrahydrofuran → HCID 88206349, compound

HRID 744864Notes

Reaction equation

HRID 744864 reaction equation
[CH:1]([NH:3][CH:4]1[C:29](=[O:30])[N:6]2[C:7]([C:13]([O:15][CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:14])=[C:8]([CH2:11][OH:12])[CH2:9][S:10][C@H:5]12)=[O:2].[NH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.[O:37]1CCC[CH2:38]1>>[CH:1]([NH:3][CH:4]1[C:29](=[O:30])[N:6]2[CH:7]([C:13]([O:15][CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[O:14])[C:8]([CH2:11][O:12][C:38]([N:31]3[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:37])=[CH:9][S:10][C@H:5]12)=[O:2]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 8082Piperidine2×HCID 15280631HCID 15280631, compound

Product 1

HCID 88206349HCID 88206349, compound

Procedure

To a solution of benzhydryl 7-formamido-3-hydroxymethyl-3-cephem-4-carboxylate (4.24 g) in tetrahydrofuran (80 ml), N,N'-carbonyldiimidazole (1.62 g) was added under ice cooling, followed by stirring at the same temperature for 1 hour and 25 minutes. Then, the resulting solution was added with a solution of piperidine (0.85 g) in tetrahydrofuran (10 ml) and stirred at the same temperature for 1 hour and 20 minutes. Further stirring was conducted for one hour at room temperature. The reaction mixture was added with piperidine (0.17 g), followed by stirring at room temperature for 11 hours and 10 minutes and then, the resulting reaction mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate. The resulting solution was washed successively with 1N hydrochloric acid, water and a saturated aqueous chloride solution, followed by drying over magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column, whereby benzhydryl 7-formamido-3-(1-piperidinyl)carbonyloxymethyl-2-cephem-4-carboxylate (2.3 g, 43.0%).

Workup

  1. stirringstirred at the same temperature for 1 hour and 20 minutes
  2. stirringFurther stirring
  3. waitwas conducted for one hour at room temperature
  4. stirringby stirring at room temperature for 11 hours and 10 minutes
  5. customthe resulting reaction mixture
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washThe resulting solution was washed successively with 1N hydrochloric acid, water
  9. dry with materialby drying over magnesium sulfate
  10. distillationThen, the solvent was distilled off under reduced pressure
  11. customThe residue was purified by chromatography on a silica gel column, whereby benzhydryl 7-formamido-3-(1-piperidinyl)carbonyloxymethyl-2-cephem-4-carboxylate (2.3 g, 43.0%)

Sources & evidence

ORD record
ord-bb5b416b5e1e4d7e9018d7b8b732b38b
Source dataset
uspto-grants-1996_09
Patent number
US05559225

Reaction notes

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