Benzaldehyde → Benzhydryl 7-Benzylideneamino-3-triphenylphosphoniomethyl-3-cephem-4-carboxylate chloride

HRID 255971Notes

Reaction equation

HRID 255971 reaction equation
Cl.[NH2:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH2:10][Cl:11])[CH2:8][S:9][C@H:4]12.[OH-].[Na+].[O-]S([O-])(=O)=O.[Mg+2].[CH:38](=O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[C:46]1([P:52]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(Cl)Cl>[Cl-:11].[CH:38](=[N:2][CH:3]1[C:28](=[O:29])[N:5]2[C:6]([C:12]([O:14][CH:15]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[O:13])=[C:7]([CH2:10][P+:52]([C:53]3[CH:54]=[CH:55][CH:56]=[CH:57][CH:58]=3)([C:59]3[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=3)[C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[CH2:8][S:9][C@H:4]12)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

7

Reactant 5

HCID 240BenzaldehydeHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 13239629Benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride

Product 1

HCID 131715334Benzhydryl 7-Benzylideneamino-3-triphenylphosphoniomethyl-3-cephem-4-carboxylate chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of diphenylmethyl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride (200 g, 0.44 mole) in CH2Cl2 (940 ml) was added 1N NaOH (440 ml) at room temperature. The mixture was shaken for 10 minutes and the organic layer was separated. To this organic layer were added MgSO4 (75 g) and benzaldehyde (51 g, 0.48 mole) and the mixture was allowed to stand for 3 hours at room temperature. The reaction mixture was filtered and the insolubles were washed with CH2Cl2 (200 ml). To the combined filtrate and washings was added triphenylphosphine (126 g, 0.48 mole). The mixture was concentrated to about 400 ml under reduced pressure and allowed to stand for 4 days. The resulting viscous oil was diluted with ethyl acetate (1 l) and triturated to separate the title compound, a pale yellow crystalline powder which was collected by filtration and dried in vacuo. Yield 322 g (96 %). M.p. 185°~190° C. (dec.).

Workup

  1. customthe organic layer was separated
  2. waitto stand for 3 hours at room temperature
  3. filtrationThe reaction mixture was filtered
  4. washthe insolubles were washed with CH2Cl2 (200 ml)
  5. concentrationThe mixture was concentrated to about 400 ml under reduced pressure
  6. waitto stand for 4 days
  7. additionThe resulting viscous oil was diluted with ethyl acetate (1 l)
  8. customtriturated
  9. customto separate the title compound
  10. filtrationa pale yellow crystalline powder which was collected by filtration
  11. customdried in vacuo

Sources & evidence

ORD record
ord-b560408f4bff4995b906b4f08190bc38
Source dataset
uspto-grants-1987_10
Patent number
US04699979

Reaction notes

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