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

HRID 580210Notes

Reaction equation

HRID 580210 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 benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride (II 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 the organic layer were added MgSO4 (75 g) and benzaldehyde (51 g, 0.48 mole) and the mixture was allowed to stand for 3 hours. 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 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 XV 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
  3. filtrationThe reaction mixture was filtered
  4. washthe insolubles were washed with CH2Cl2 (200 ml)
  5. concentrationThe mixture was concentrated to about 400 ml
  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 XV a pale yellow crystalline powder which
  10. filtrationwas collected by filtration
  11. customdried in vacuo

Sources & evidence

ORD record
ord-22d13a9418e54e1a818781c53935bd9a
Source dataset
uspto-grants-1988_06
Patent number
US04751295

Reaction notes

Loading…