Pyridine → HCID 70524728, compound

HRID 1902518Notes

Reaction equation

HRID 1902518 reaction equation
N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.C1(CC([NH:22][CH:23]2[C:48](=[O:49])[N:25]3[CH:26]([C:35]([O:37][CH2:38][C:39]4[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=4)=[O:36])[C:27](=[CH:30][O:31][C:32](=[O:34])[CH3:33])[CH2:28][S:29][C@H:24]23)=O)C=CC=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.CO>[NH2:22][CH:23]1[C:48](=[O:49])[N:25]2[CH:26]([C:35]([O:37][CH2:38][C:39]3[CH:44]=[CH:43][C:42]([N+:45]([O-:47])=[O:46])=[CH:41][CH:40]=3)=[O:36])[C:27](=[CH:30][O:31][C:32](=[O:34])[CH3:33])[CH2:28][S:29][C@H:24]12

Participants

8

Reactant 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 70524504HCID 70524504, compound

Product 1

HCID 70524728HCID 70524728, compoundYield 71.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Pyridine (1.2 g.) was added to a solution of phosphorus pentachloride (3.1 g.) in methylene chloride (30 ml.) at 5° to 7° C. and stirred at the same temperature for 30 minutes. To the solution was added 4-nitrobenzyl 7-(2-phenylacetamido)-3-acetoxymethylenecepham-4-carboxylate (5.4 g.) at -10° C., and stirred at the same temperature for 1.5 hours. Methanol (8 ml.) was added to the solution at -30° C. and stirred at 0° C. for 40 minutes. Water (10 ml.) and methylene chloride (50 ml.) were added to the solution and adjusted to pH 5.0 with an aqueous solution of sodium bicarbonate. The organic layer was separated, washed with water (30 ml×2) and adjusted to pH 7.5 with an aqueous solution of sodium bicarbonate. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over magnesium sulfate. After treating the solution with activated charcoal, the solution was evaporated under reduced pressure. The residue was pulverized with diisopropyl ether and the precipitates were collected by filtration to give 4-nitrobenzyl 7-amino-3-acetoxymethylenecepham-4-carboxylate (3.0 g.).

Workup

  1. stirringstirred at the same temperature for 1.5 hours
  2. stirringstirred at 0° C. for 40 minutes
  3. customThe organic layer was separated
  4. washwashed with water (30 ml×2)
  5. customThe organic layer was separated
  6. washwashed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. additionAfter treating the solution with activated charcoal
  9. customthe solution was evaporated under reduced pressure
  10. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-a41a291126604ebcbafedb122233bc24
Source dataset
uspto-grants-1982_12
Patent number
US04363807

Reaction notes

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