Pyridine → HCID 67899263, compound

HRID 1681452Notes

Reaction equation

HRID 1681452 reaction equation
C1(CC([NH:10][CH:11]2[C:37](=[O:38])[N:13]3[C:14]([C:21]([O:23][CH:24]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]23)=O)C=CC=CC=1.N1C=CC=CC=1.P(Cl)(Cl)(Cl)(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl.CO>[NH2:10][CH:11]1[C:37](=[O:38])[N:13]2[C:14]([C:21]([O:23][CH:24]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[O:22])=[C:15](/[CH:18]=[CH:19]\[CH3:20])[CH2:16][S:17][C@H:12]12

Participants

7

Reactant 4

HCID 1049PyridineHCID 24819Phosphorus pentachlorideHCID 516892Sodium BicarbonateHCID 13938977HCID 13938977, compound

Product 1

HCID 67899263HCID 67899263, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-40 °C

Procedure

6.4 (12.2 mmol) of benzhydryl 7-phenylacetamido-3-[(Z)-propen-1-yl]-3-cephem-4-carboxylate (Example 9) are dissolved in 64 ml of methylene chloride, the solution is cooled to -40° C. with a dry ice bath and 2.47 ml (30.5 mmol) of pyridine and 2.54 g (12.2 mmol) of phosphorus pentachloride are added in succession. After 5 minutes, the mixture is allowed to warm to -20° C., after which the temperature should rise to -10° C. in the course of 20 minutes and then rise to +10° C. The solution is now stirred at +10° C. to +15° C. for 1 hour. The mixture is subsequently cooled to -40° C., 100 ml of methanol (-30° C.) are added and the mixture is stirred at +10° C. for a further 30 minutes. The reaction solution is concentrated gently, the oil obtained is dissolved in 600 ml of methylene chloride, the solution is stirred into 800 ml of sodium bicarbonate solution and the mixture is stirred for 10 minutes. The methylene chloride phase is separated off, washed once with water and dried over sodium sulphate. The methylene chloride filtrate is chromatographed on 400 ml of silica gel (0.04-0.063 mm), elution being carried out first with methylene chloride and then with methylene chloride with the addition of methanol (gradient up to 10%). The eluate is investigated by means of analytical HPLC and TLC (thin layer chromatography) (methylene chloride/methanol=100:1).

Workup

  1. temperatureto warm to -20° C.
  2. customshould rise to -10° C. in the course of 20 minutes
  3. customrise to +10° C
  4. temperatureThe mixture is subsequently cooled to -40° C.
  5. stirringthe mixture is stirred at +10° C. for a further 30 minutes
  6. concentrationThe reaction solution is concentrated gently
  7. customthe oil obtained
  8. stirringthe mixture is stirred for 10 minutes
  9. customThe methylene chloride phase is separated off
  10. washwashed once with water
  11. dry with materialdried over sodium sulphate
  12. customThe methylene chloride filtrate is chromatographed on 400 ml of silica gel (0.04-0.063 mm), elution
  13. additionwith methylene chloride with the addition of methanol (gradient up to 10%)

Sources & evidence

ORD record
ord-1f343bfc46364d6490beb9daad7b7cd0
Source dataset
uspto-grants-1992_12
Patent number
US05171854

Reaction notes

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