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

HRID 255972Notes

Reaction equation

HRID 255972 reaction equation
[Cl-].[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.C([O-])([O-])=O.[Na+].[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 10340Sodium CarbonateHCID 131715334Benzhydryl 7-Benzylideneamino-3-triphenylphosphoniomethyl-3-cephem-4-carboxylate chloride

Product 1

HCID 13938965Benzhydryl 7-Benzylideneamino-3-[(triphenylphosphoranylidene)methyl]-3-cephem-4-carboxylateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of diphenylmethyl 7-benzylideneamino-3-triphenylphosphoniomethyl-3-cephem-4-carboxylate chloride (322 g, 0.42 mole) and 5N Na2CO3 (252 ml) in CH2Cl2 (1.6 l) was stirred vigorously for 15 minutes at room temperature. The organic layer was separated, dried over MgSO4 and concentrated to about 500 ml of volume. The concentrate was diluted with acetone (1 l), with stirring, to give a light yellow crystalline powder which was collected by filtration to yield 237 g (78%) of III, melting at 195°~198° C. (dec.).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated to about 500 ml of volume
  4. additionThe concentrate was diluted with acetone (1 l)
  5. stirringwith stirring
  6. customto give a light yellow crystalline powder which
  7. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-c4f1ad24bb2d464e976d4de5b8d7534b
Source dataset
uspto-grants-1987_10
Patent number
US04699979

Reaction notes

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