Tetrahydrofuran → HCID 88206349, compound

HRID 864623Notes

Reaction equation

HRID 864623 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

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

Sources & evidence

ORD record
ord-a3a9d60885ac4c5da6d7fbc4afdece05
Source dataset
uspto-grants-1996_10
Patent number
US05563265

Reaction notes

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