Sodium Hydroxide → Benzhydryl 7-Benzylideneamino-3-[(triphenylphosphoranylidene)methyl]-3-cephem-4-carboxylate

HRID 580208Notes

Reaction equation

HRID 580208 reaction equation
[I-].[CH:2](=[N:9][CH:10]1[C:53](=[O:54])[N:12]2[C:13]([C:37]([O:39][CH:40]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[O:38])=[C:14]([CH2:17][P+:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][S:16][C@H:11]12)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[OH-].[Na+]>C(Cl)Cl>[CH:2](=[N:9][CH:10]1[C:53](=[O:54])[N:12]2[C:13]([C:37]([O:39][CH:40]([C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)=[O:38])=[C:14]([CH:17]=[P:18]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][S:16][C@H:11]12)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 88469401Diphenylmethyl 7-benzylideneamino-3-[(triphenylphosphonio)methyl]-3-cephem-4-carboxylate iodide

Product 1

HCID 13938965Benzhydryl 7-Benzylideneamino-3-[(triphenylphosphoranylidene)methyl]-3-cephem-4-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

To a solution of diphenylmethyl 7-benzylideneamino-3-[(triphenylphosphonio)methyl]-3-cephem-4-carboxylate iodide (XV) [prepared according to the procedure of Japan published patent application (Kokai) No. 56-86187 (7/31/81)] (60 g, 70 mmole) in CH2Cl2 (350 ml) were added N NaOH (140 ml) and Amberlite IRA-410 (OH- form, 35 g) at 5° C. The mixture was stirred for 1 hour at 5° C. and filtered. The organic layer was separated, dried over MgSO4, concentrated to ca. 100 ml of volume and precipitated with ethyl acetate (500 ml). The resulting yellow solid was collected by filtration and dried in vacuo to afford 48 g (94%) of the title compound XVI, melting at 195°-8° C. (dec.).

Workup

  1. filtrationfiltered
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to ca. 100 ml of volume
  5. customprecipitated with ethyl acetate (500 ml)
  6. filtrationThe resulting yellow solid was collected by filtration
  7. customdried in vacuo

Sources & evidence

ORD record
ord-d5fcc2762ec448f3933ecc5ccb4804a8
Source dataset
uspto-grants-1988_06
Patent number
US04751295

Reaction notes

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