Isopropanol → Benzhydryl 7-salicylideneamino-3-vinyl-3-cephem-4-carboxylate

HRID 569372Notes

Reaction equation

HRID 569372 reaction equation
[CH:1](=[N:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:14]([CH2:17]Cl)[CH2:15][S:16][C@H:11]12)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].[C:37]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I-].[Na+].C(O)(C)C>CN(C)C=O>[CH:1](=[N:9][CH:10]1[C:35](=[O:36])[N:12]2[C:13]([C:19]([O:21][CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:14]([CH:17]=[CH2:37])[CH2:15][S:16][C@H:11]12)[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 5238Sodium IodideHCID 11776TriphenylphosphineHCID 136460599Benzhydryl 7-salicylideneamino-3-chloromethyl-3-cephem-4-carboxylate

Product 1

HCID 136460592Benzhydryl 7-salicylideneamino-3-vinyl-3-cephem-4-carboxylateYield 78.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled solution of benzhydryl 7-salicylideneamino-3-chloromethyl-3-cephem-4-carboxylate (4 g) in dimethylformamide (10 ml) were added triphenylphosphine (2.2 g) and sodium iodide with stirring. After stirring for 2 hours at ambient temperature, the reaction mixture was poured into isopropyl alcohol (250 ml), and the precipitated solids (6.7 g) were collected by filtration. To a stirred solution of the above solids in methylene chloride (10 ml) and water (5 ml) was added 36% formaldehyde solution (17.4 ml). Then the reaction mixture was adjusted to pH 9.0 with a saturated aqueous sodium bicarbonate. After stirring for an hour at ambient temperature, the separated organic layer was washed with water and an aqueous sodium chloride, followed by drying over magnesium sulfate. The solution was evaporated under reduced pressure to give benzhydryl 7-salicylideneamino-3-vinyl-3-cephem-4-carboxylate (3 g).

Workup

  1. stirringAfter stirring for 2 hours at ambient temperature
  2. filtrationthe precipitated solids (6.7 g) were collected by filtration
  3. additionTo a stirred solution of the above solids in methylene chloride (10 ml) and water (5 ml) was added 36% formaldehyde solution (17.4 ml)
  4. stirringAfter stirring for an hour at ambient temperature
  5. washthe separated organic layer was washed with water
  6. dry with materialby drying over magnesium sulfate
  7. customThe solution was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5805949f6a834d9ea59e59ff7be8a1b0
Source dataset
uspto-grants-1988_03
Patent number
US04731443

Reaction notes

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